1-dimethylamino-non-1-en-3-one | 63859-48-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-dimethylamino-non-1-en-3-one
• 英文别名: 1-(Dimethylamino)non-1-EN-3-one
• CAS: 63859-48-3
• 化学式: C₁₁H₂₁NO
• 分子量: 183.294
• InChiKey: CHJVYZKLDXMEPT-UHFFFAOYSA-N

物化性质

• 沸点：
  131-132 °C(Press: 1.5 Torr)
• 密度：
  0.9092 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-dimethylamino-non-1-en-3-one 在 1-碘丁烷 作用下， 以 乙醚 为溶剂， 生成 (E)-tridec-5-en-7-one
  参考文献：
  名称：

  Tishchenko,I.G. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1062 - 1066

  摘要：

  DOI：
• 作为产物：
  描述：

  1-chloro-non-1-en-3-one 、 二甲胺 生成 1-dimethylamino-non-1-en-3-one
  参考文献：
  名称：

  Tishchenko,I.G. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1062 - 1066

  摘要：

  DOI：

文献信息

• Mn(OAc)₃-Promoted Oxidative C_sp³–P Bond Formation through C_sp²–C_sp² and P–H Bond Cleavage: Access to β-Ketophosphonates
  作者：Pan Zhou、Biao Hu、Lingdan Li、Kairui Rao、Jiao Yang、Fuchao Yu

  DOI：10.1021/acs.joc.7b02391

  日期：2017.12.15

  The Mn(OAc)3-promoted oxidative phosphonylation of N,N-dimethylenaminones with H-phosphonates, involving a chemo- and regioselective Csp2–Csp2 bond cleavage and Csp3–P bond formation in one step, provided successfully functionalized β-ketophosphonates under mild reaction conditions. Oxidative Csp3–H/P–H cross-coupling reactions via Csp3–C(C═O) bond cleavage and mechanistic studies are conducted preliminarily

  Mn（OAc）3促进N，N-二甲基亚氨基酮与H-膦酸酯的氧化膦酰化作用，涉及化学和区域选择性C sp 2 –C sp 2键断裂和C sp 3 –P键形成的一步，成功提供在温和的反应条件下官能化的β-酮膦酸酯。通过C sp 3氧化C sp 3 –H / P–H交叉偶联反应初步进行了-C（C═O）键的裂解和机理研究，并提出了可能的机理。这种新颖的方法以良好的收率获得了良好的收率，显示出操作简便性，广泛的底物范围和大规模的制备方法。
• Prostaglandin intermediates
  申请人：Ayerst McKenna and Harrison Ltd.

  公开号：US04006136A1

  公开（公告）日：1977-02-01

  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 PCCH.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 borehydride 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 CaC 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 cyclopentanone-triester 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 the 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.

  本发明提供了一种制备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-(可选取代)-2-甲酰基环丙烷-1,1-二羧酸酯与由Wittig试剂制备的ylid反应，该Wittig试剂的化学式为(AlkO).sub.2 PCCH.sub.2 CO-(c)-CH.sub.3，其中Alk是含有一到三个碳原子的烷基，(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，其化学式为：##STR1## 其中R.sup.2是氢、低烷基或CH.sub.2 OR.sup.3，其中R.sup.3是低烷酰基，R.sup.4是低烷基，(c)如上所定义。后一种化合物与碱金属硼氢化物还原，得到相应的醇衍生物。该醇衍生物或更好的是其相应的四氢吡喃-2-基醚衍生物与化学式为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CaC，p是2至4的整数，得到相应的环戊酮三酯化合物，其化学式为：##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环戊酮三酯的内酯形式，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，得到相应的化合物，其中R.sup.5为氢。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，得到所需的化学式为：##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为氢或低烷酰基，R.sup.2为氢、低烷基或CH.sub.2 OR.sup.3，其中R.sup.3为氢或低烷酰基。这些衍生物具有前列腺素类似的生物活性，并提供了其使用方法。
• 11-Deoxyprostaglandin derivatives
  申请人：Ayerst, McKenna & Harrison Limited

  公开号：US04100343A1

  公开（公告）日：1978-07-11

  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 akyl 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 cyclopentanone-triester 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.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 method for their use are given.

  本发明涉及一种制备11-去氧前列腺素E.sub.1，E.sub.2和E.sub.3及其类似物的过程，通过将适当的二（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Wittig试剂制备的ylid反应，所述Wittig试剂的化学式为（AlkO）.sub.2 POCH.sub.2 CO-(c)-CH.sub.3，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.dbd.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式子：##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。后者的化合物经过碱金属硼氢化物还原后，得到相应的醇衍生物。将该醇衍生物或者更好的是其相应的四氢吡喃-2-基醚衍生物与化学式为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，顺式CH.dbd.CH或C.tbd.C，p是2至4的整数，得到相应的环戊酮三酯的化学式：##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环戊酮三酯的内酯形式，其中R.sup.2为CH.sub.2 OR.sup.3，其中R.sup.3为低脂肪酰基。在R.sup.5为四氢吡喃-2-基时，将环戊酮三酯处理成R.sup.5为氢的相应化合物。然后在水溶液条件下将瞬时化合物处理成碱，随后进行可选的酯化和酰化，以得到所需的化学式为：##STR3## 其中（a），（c）和p如上所定义，（b）为顺式CH.dbd.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为氢或低脂肪酰基的11-去氧前列腺素衍生物。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。
• Copper-Catalyzed Oxidative [3 + 2] Cycloaddition of Enamines and Pyridotriazoles toward Indolizines
  作者：Enfu Wang、Jiangbin Luo、Luoman Zhang、Jian Zhang、Yaojia Jiang

  DOI：10.1021/acs.orglett.4c00063

  日期：2024.2.16

  catalytic system has been established for the synthesis of highly functional indolizines through oxidative [3 + 2] cycloaddition of enamines and pyridotriazoles. This modular platform is compatible with a broad range of functional groups, including natural and complex skeletons, allowing for late-stage modifications. It features a step-economical, highly regioselective, and easy-handling procedure and has been

  建立了一种高效的铜催化体系，用于通过烯胺和吡啶并三唑的氧化[3+2]环加成合成高功能中氮茚。该模块化平台与广泛的功能组兼容，包括自然和复杂的骨架，允许后期修改。它具有步骤经济、高度区域选择性和易于操作的特点，并已被应用于构建具有有效活性的小分子，通过吡啶并三唑、胺和醛的一锅反应抑制 VEGF-NRP1 相互作用。
• Tishchenko,I.G. et al., Journal of Organic Chemistry USSR (English Translation), 1977, vol. 13, p. 1062 - 1066
  作者：Tishchenko,I.G. et al.

  DOI：——

  日期：——