Trimethyl-cis-3-hepten-1,1,7-tricarboxylat | 41502-74-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Trimethyl-cis-3-hepten-1,1,7-tricarboxylat
• 英文别名: trimethyl cis-3-heptene-1,1,7-tricarboxylate；Trimethyl cis-3-heptene-1,1,7-tricarboxylate；trimethyl (Z)-hept-3-ene-1,1,7-tricarboxylate
• CAS: 41502-74-3
• 化学式: C₁₃H₂₀O₆
• 分子量: 272.298
• InChiKey: GIBOKUSEZDIJKT-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Trimethyl-cis-3-hepten-1,1,7-tricarboxylat 、 Dimethyl trans-2(3-Hydroxy-1-octenyl)cyclopropane-1,1-dicarboxylate 在 sodium methylate 作用下， 生成 3-Acetoxy-5-((E)-3-hydroxy-oct-1-enyl)-1-((Z)-6-methoxycarbonyl-hex-2-enyl)-2-oxo-cyclopentanecarboxylic acid methyl ester
  参考文献：
  名称：

  Prostaglandin VI - an efficient synthesis of II-desoxyprostaglandins

  摘要：

  DOI：

  10.1016/s0040-4039(01)95833-2
• 作为产物：
  描述：

  Trimethyl 3-heptyne-1,1,7-tricarboxylate 以 正己烷 、 3,6-二硫杂-1,8-辛二醇 、 乙酸乙酯 为溶剂， 生成 Trimethyl-cis-3-hepten-1,1,7-tricarboxylat
  参考文献：
  名称：

  Prostaglandin intermediates

  摘要：

  该过程是通过将适当的二(低)烷基3-(可选择取代)-2-甲醛环丙烷-1,1-二羧酸酯与由Wittig试剂制备的具有化学式(AlkO).sub.2PCCH.sub.2CO-(c)-CH.sub.3的偏磷酸酯反应来制备11-去氧前列腺素E.sub.1、E.sub.2和E.sub.3及其类似物。其中，Alk是含有一到三个碳原子的烷基，(c)可以是(CH.sub.2).sub.q，其中q是从1到6的整数，或者是顺式CH.sub.2CH=CH(CH.sub.2).sub.r，其中r是从0到3的整数，从而得到相应的化合物，其化学式为： 在这个化合物中，R.sup.2是氢、低烷基或CH.sub.2OR.sup.3，其中R.sup.3是低烷酰基，R.sup.4是低烷基，(c)如本文所定义。后一种化合物经碱金属硼氢化物还原得到相应的醇衍生物。将这种醇衍生物或更好地是其相应的四氢吡喃-2-基醚衍生物与具有化学式CH(COOR.sup.6).sub.2-(a)-(CH.sub.2)pCOOR的三酯缩合，其中R和R.sup.6是低烷基，(a)是CH.sub.2CH.sub.2、顺式CH=CH或CaC，p是从2到4的整数，得到相应的环戊酮三酯，其化学式为： 其中(a)、(c)、p、R、R.sup.4和R.sup.6如本文所定义，R.sup.5是氢或四氢吡喃-2-基，R.sup.7是氢或低烷基；环戊酮三酯的内酯形式可从上述R.sup.2为CH.sub.2OR.sup.3的醇衍生物中得到，其中R.sup.3是低烷酰基。当R.sup.5为四氢吡喃-2-基时，环戊酮三酯经酸处理得到R.sup.5为氢的相应化合物。然后，将该化合物在水性条件下处理碱，随后进行可选择的酯化和酰化，得到所需的11-去氧前列腺素衍生物，其化学式为： 其中(a)、(c)和p如本文所定义，(b)为顺式CH=CH，R是氢或低烷基，R.sup.1是氢或低烷酰基，R.sup.2是氢、低烷基或CH.sub.2OR.sup.3，其中R.sup.3是氢或低烷酰基。这些衍生物具有类似前列腺素的生物活性，并提供了它们的使用方法。

  公开号：

  US04006136A1

文献信息

• 11 Hydroxy methyl 11-deoxyprostaglandin E.sub.1
  申请人：Ayerst, McKenna and Harrison Limited

  公开号：US04161608A1

  公开（公告）日：1979-07-17

  A process for preparing 11-deoxyprostaglandin E.sub.1, E.sub.2 and E.sub.3 and analogs thereof is realized by treating an appropriate di(lower)alkyl 3-(optionally substituted)-2-formylcyclopropane-1,1-dicarboxylate with an ylid prepared from a Wittig reagent of formula (AlkO).sub.2 POCH.sub.2 CO--(c)-CH.sub.3 in which Alk is an alkyl containing one to three carbon atoms and (c) is either (CH.sub.2).sub.q wherein q is an integer from 1 to 6 or cis CH.sub.2 CH.dbd.CH(CH.sub.2).sub.r wherein r is an integer from 0 to 3 to obtain the corresponding compound of formula: ##STR1## in which R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl, R.sup.4 is lower alkyl and (c) is as defined herein. The latter compound is reduced with an alkali metal borohydride to yield the corresponding alcohol derivative. Condensation of this alcohol derivative or preferably its corresponding tetrahydropyran-2-yl ether derivative with a triester of formula CH(COOR.sup.6).sub.2 --(a)-(CH.sub.2)pCOOR in which R and R.sup.6 are lower alkyl, (a) is CH.sub.2 CH.sub.2, cis CH.dbd.CH or C.tbd.C and p is an integer from 2 to 4, gives the corresponding cyclopentanonetriester of formula ##STR2## in which (a), (c), p, R, R.sup.4 and R.sup.6 are as defined herein, R.sup.5 is hydrogen or tetrahydropyran-2-yl, respectively, and R.sup.7 is hydrogen or lower alkyl; the lactonized form of the cyclopentanonetriester being obtained from said alcohol derivative in which R.sup.2 is CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl. In the instance when R.sup.5 is tetrahydropyran-2-yl the cyclopentanonetriester is treated with an acid to give the corresponding compound in which R.sup.5 is hydrogen. The instant compound is then treated with a base under aqueous conditions, followed by optional esterification and acylation to give the desired 11-deoxy-prostaglandin derivatives of formula ##STR3## in which (a), (c) and p, are as defined herein, (b) is trans CH.dbd.CH, R is hydrogen or lower alkyl, R.sup.1 is hydrogen or lower alkanoyl and R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is hydrogen or lower alkanoyl. The derivatives possess prostaglandin-like biological activity and methods for their use are given.

  一种制备11-去氧前列腺素E.sub.1，E.sub.2和E.sub.3及其类似物的方法，通过将适当的二（较低）烷基3-（可选取取代基）-2-甲酰基环丙烷-1,1-二羧酸酯与由公式（AlkO）.sub.2 POCH.sub.2 CO-制备的Wittig试剂的ylid处理，其中Alk是含有1至3个碳原子的烷基，（c）是（CH.sub.2）.sub.q，其中q是1至6的整数，或者是顺式CH.sub.2 CH=CH（CH.sub.2）.sub.r，其中r是0至3的整数，以得到相应的化合物的公式：##STR1## 其中R.sup.2是氢，较低的烷基或CH.sub.2 OR.sup.3，其中R.sup.3是较低的烷酰基，R.sup.4是较低的烷基，（c）如上所定义。后一种化合物用碱金属硼氢化物还原，得到相应的醇衍生物。将此醇衍生物或者更好的是其相应的四氢吡喃-2-基醚衍生物与公式CH（COOR.sup.6）.sub.2 --（a）-（CH.sub.2）pCOOR的三酯缩合，其中R和R.sup.6是较低的烷基，（a）是CH.sub.2 CH.sub.2，顺式CH=CH或C.tbd.C，p是2至4的整数，得到相应的环戊烷三酯的公式：##STR2## 其中（a），（c），p，R，R.sup.4和R.sup.6如上所定义，R.sup.5分别为氢或四氢吡喃-2-基，R.sup.7为氢或较低的烷基；从所述醇衍生物中得到环戊烷三酯的内酯形式，其中R.sup.2为CH.sub.2 OR.sup.3，其中R.sup.3为较低的烷酰基。当R.sup.5为四氢吡喃-2-基时，用酸处理环戊烷三酯，得到相应的化合物，其中R.sup.5为氢。然后在水性条件下将瞬时化合物处理为碱，随后进行可选的酯化和酰化，得到所需的公式：##STR3## 其中（a），（c）和p如上所定义，（b）为顺式CH=CH，R为氢或较低的烷基，R.sup.1为氢或较低的烷酰基，R.sup.2为氢，较低的烷基或CH.sub.2 OR.sup.3，其中R.sup.3为氢或较低的烷酰基。这些衍生物具有类似前列腺素的生物活性，并提供了其使用方法。
• Alkyl derivatives of prostanoic acids and preparation thereof
  申请人：American Home Products Corporation

  公开号：US03987081A1

  公开（公告）日：1976-10-19

  15- And/or 16-alkyl derivatives of 9,15-dioxygenated prost-13-enoic, prosta-4,13-dienoic and prosta-5,13-dienoic acid, lower alkyl esters thereof and homologs thereof, as well as a process for preparing these derivatives are disclosed. The compounds possess hypotensive, antihypertensive, bronchospasmolytic, gastric acid secretion inhibiting, abortifacient, estrus synchronizing and ovulation regulating properties. The compounds also inhibit the aggregation of platelets and promote the disaggregation of aggregated platelets. Methods for their use are also disclosed.

  本文介绍了9,15-二氧代前列腺-13-烯酸、前列腺-4,13-二烯酸和前列腺-5,13-二烯酸的15-和/或16-烷基衍生物、其较低的烷基酯和同系物，以及制备这些衍生物的方法。这些化合物具有降压、抗高血压、支气管痉挛解除、抑制胃酸分泌、引产、发情同步和排卵调节的特性。这些化合物还能抑制血小板的聚集并促进已聚集的血小板的分散。本文还介绍了它们的使用方法。
• Intermediates for prostanoic acids
  申请人：American Home Products Corporation

  公开号：US04007171A1

  公开（公告）日：1977-02-08

  15- And/or 16-alkyl derivatives of 9,15-dioxygenated prost-13-enoic, prosta-4,13-dienoic and prosta-5,13-dienoic acid, lower alkyl esters thereof and homologs thereof, as well as a process for preparing these derivatives are disclosed. The compounds possess hypotensive, antihypertensive, bronchospasmolytic, gastric acid secretion inhibiting, abortifacient, estrus synchronizing and ovulation regulating properties. The compounds also inhibit the aggregation of platelets and promote the disaggregation of aggregated platelets. Methods for their use are also disclosed.

  本文披露了9,15-二氧代前列腺-13-烯酸、前列腺-4,13-二烯酸和前列腺-5,13-二烯酸的15-和/或16-烷基衍生物，以及其较低的烷基酯和同系物，以及制备这些衍生物的方法。这些化合物具有降压、抗高血压、支气管痉挛解除、抑制胃酸分泌、引产、发情同步和促排卵的特性。这些化合物还能抑制血小板聚集并促进聚集血小板的解聚。同时，本文还披露了它们的使用方法。
• Cyclopentanone derivatives
  申请人：Ayerst McKenna and Harrison Ltd.

  公开号：US04036856A1

  公开（公告）日：1977-07-19

  A process for preparing 11-deoxyprostaglandin E.sub.1, E.sub.2 and E.sub.3 and analogs thereof is realized by treating an appropriate di(lower)alkyl 3-(optionally substituted)-2-formylcyclopropane-1,1-dicarboxylate with an ylid prepared from a Wittig reagent of formula (AlkO).sub.2 POCH.sub.2 CO-(c)-CH.sub.3 in which Alk is an alkyl containing one to three carbon atoms and (c) is either (CH.sub.2).sub.q wherein q is an integer from 1 to 6 or cis CH.sub.2 CH=CH(CH.sub.2).sub.r wherein r is an integer from 0 to 3 to obtain the corresponding compound of formula: ##STR1## in which R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl, R.sup.4 is lower alkyl and (c) is as defined herein. The latter compound is reduced with an alkali metal borohydride to yield the corresponding alcohol derivative. Condensation of this alcohol derivative or preferably its corresponding tetrahydropyran-2-yl ether derivative with a triester of formula CH(COOR.sup.6).sub.2 --(a)-(CH.sub.2)pCOOR in which R and R.sup.6 are lower alkyl, (a) is CH.sub.2 CH.sub.2, cis CH=CH or C.tbd.C and p is an integer from 2 to 4, gives the corresponding cyclopentanonetriester of formula ##STR2## in which (a), (c), p, R, R.sup.4 and R.sup.6 are as defined herein, R.sup.5 is hydrogen or tetrahydropyran-2-yl, respectively, and R.sup.7 is hydrogen or lower alkyl; the lactonized form of the cyclopentanonetriester being obtained from said alcohol derivative in which R.sup.2 is CH.sub.2 OR.sup.3 wherein R.sup.3 is lower alkanoyl. In the instance when R.sup.5 is tetrahydropyran-2-yl the cyclopentanonetriester is treated with an acid to give the corresponding compound in which R.sup.5 is hydrogen. The instant compound is then treated with a base under aqueous conditions, followed by optional esterification and acylation to give the desired 11-deoxyprostaglandin derivatives of formula ##STR3## in which (a), (c) and p, are as defined herein, (b) is trans CH=CH, R is hydrogen or lower alkyl, R.sup.1 is hydrogen or lower alkanoyl and R.sup.2 is hydrogen, lower alkyl or CH.sub.2 OR.sup.3 wherein R.sup.3 is hydrogen or lower alkanoyl. The derivatives possess prostaglandin-like biological activity and methods for their use are given.

  一种制备11-去氧前列腺素E.sub.1，E.sub.2和E.sub.3及其类似物的方法，通过处理适当的二（较低）烷基3-（可选地取代的）2-甲酰基环丙烷-1,1-二羧酸酯与由公式（AlkO）.sub.2 POCH.sub.2 CO-（c）-CH.sub.3的Wittig试剂制备的ylid反应，其中Alk是含有1至3个碳原子的烷基，（c）是（CH.sub.2）.sub.q，其中q是1至6的整数，或cis CH.sub.2 CH=CH（CH.sub.2）.sub.r，其中r是0至3的整数，以获得相应的化合物的公式：##STR1##其中R.sup.2是氢，低烷基或CH.sub.2 OR.sup.3，其中R.sup.3是低脂肪酰基，R.sup.4是低烷基，（c）如上所定义。后一化合物通过碱金属硼氢化物还原，得到相应的醇衍生物。将该醇衍生物或其相应的四氢吡喃-2-基醚衍生物与公式CH（COOR.sup.6）.sub.2-（a）-（CH.sub.2）pCOOR的三酯缩合，其中R和R.sup.6是低烷基，（a）是CH.sub.2 CH.sub.2，cis CH=CH或C.tbd.C，p是2至4的整数，得到相应的环戊烷三酯的公式：##STR2##其中（a），（c），p，R，R.sup.4和R.sup.6如上所定义，R.sup.5分别为氢或四氢吡喃-2-基，R.sup.7为氢或低烷基；从所述醇衍生物中获得所述环戊烷三酯的内酯形式，其中R.sup.2是CH.sub.2 OR.sup.3，其中R.sup.3是低脂肪酰基。在R.sup.5为四氢吡喃-2-基的情况下，将环戊烷三酯处理为酸，得到相应的R.sup.5为氢的化合物。然后在水性条件下用碱处理该化合物，随后进行可选的酯化和酰化，以得到所需的公式：##STR3##其中（a），（c）和p如上所定义，（b）为trans CH=CH，R为氢或低烷基，R.sup.1为氢或低脂肪酰基，R.sup.2为氢，低烷基或CH.sub.2 OR.sup.3，其中R.sup.3为氢或低脂肪酰基。这些衍生物具有类似前列腺素的生物活性，并给出了它们的使用方法。
• Alkyl derivatives of 4,5-dehydro PGE.sub.1
  申请人：American Home Products Corporation

  公开号：US04048329A1

  公开（公告）日：1977-09-13

  15- And/or 16-alkyl derivatives of 9,15-dioxygenated prost-13-enoic, prosta-4,13-dienoic and prosta-5,13-dienoic acid, lower alkyl esters thereof and homologs thereof, as well as a process for preparing these derivatives are disclosed. The compounds possses hypotensive, antihypertensive, bronchospasmolytic, gastric acid secretion inhibiting, abortifacient, estrus synchronizing and ovulation regulating properties. The compounds also inhibit the aggregation of platelets and promote the disaggregation of aggregated platelets. Methods for their use are also disclosed.

  本文介绍了9,15-二氧代前列腺-13-烯酸、前列腺-4,13-二烯酸和前列腺-5,13-二烯酸的15-和/或16-烷基衍生物、其低烷基酯和同系物，以及制备这些衍生物的方法。这些化合物具有降压、抗高血压、支气管痉挛解除、抑制胃酸分泌、引产、发情同步和促排卵等性质。这些化合物还可以抑制血小板聚集并促进已聚集的血小板解聚。本文还介绍了它们的使用方法。