1-(dimethylamino)hex-1-en-3-one | 6135-08-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(dimethylamino)hex-1-en-3-one
• 英文别名: (CH3)2NCHCHCO(n-C3H7)；1-(Dimethylamino)-1-hexen-3-one
• CAS: 6135-08-6
• 化学式: C₈H₁₅NO
• 分子量: 141.213
• InChiKey: WDCXDDFQZVBSKY-UHFFFAOYSA-N

物化性质

• 沸点：
  120-121 °C(Press: 5 Torr)
• 密度：
  0.9339 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 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)hex-1-en-3-one 在 碘甲烷 作用下， 生成 2-methyl-3-oxo-hexanal
  参考文献：
  名称：

  Kotschetkow et al., Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1956, p. 676,678; engl. Ausg. S. 687, 688

  摘要：

  DOI：
• 作为产物：
  描述：

  6-Dimethylamino-hexadien-(2.5)-on-(4) 在 Lindlar's catalyst 氢气 作用下， 以 甲醇 为溶剂， 生成 1-(dimethylamino)hex-1-en-3-one
  参考文献：
  名称：

  Bondarev,G.N.; Petrov,A.A., Journal of Organic Chemistry USSR (English Translation), 1968, vol. 4, p. 24 - 27

  摘要：

  DOI：

文献信息

• Synthesis and Biological Activity of 2′,3′-iso-Aryl-abscisic Acid Analogs
  作者：Chuan Wan、Mingan Wang、Dongyan Yang、Xiaoqiang Han、Chuanliang Che、Shanshan Ding、Yumei Xiao、Zhaohai Qin

  DOI：10.3390/molecules22122229

  日期：——

  with three bioassays, Arabidopsis and lettuce seed germination and rice seedling elongation. Some of them, i.e., 2′,3′-iso-pyridoabscisic acid (iso-PyABA) and 2′,3′-iso-franoabscisic acid (iso-FrABA), displayed good bioactivities that closed to iso-PhABA and natural (+)-ABA. Some others, for instance, substituted-iso-PhABA, exhibited certain selectivity to different physiological process when compared

  2',3'-异苯并脱落酸 (iso-PhABA) 是一种极好的选择性脱落酸 (ABA) 类似物，是在我们之前的工作中开发的。为了找到其更多的构效信息，本文完成了一些结构修饰，包括取代苯环和用杂环取代环。因此，合成了 16 种新型的异 PhABA 类似物，并通过三种生物测定法进行了筛选，即拟南芥和莴苣种子萌发和水稻幼苗伸长。其中一些，即 2',3'-异吡啶基脱落酸 (iso-PyABA) 和 2',3'-异呋喃脱落酸 (iso-FrABA)，显示出与异 PhABA 和天然物质接近的良好生物活性。 +)-ABA。与iso-PhABA或(+)-ABA相比，其他一些，例如取代的iso-PhABA对不同的生理过程表现出一定的选择性。
• Solvent-Induced Deuterium Isotope Effects in13C- and15N-NMR. Spectra of Enaminones
  作者：Lech Kozerski、Wolfgang von Philipsborn

  DOI：10.1002/hlca.19820650715

  日期：1982.11.3

  effect of deuterium on the 13C and 15N chemical shifts of enaminones has been investigated. D/H isotope shifts are reported for neutral and protonated species, i.e., when the isotope is exchanged on the C(2)-, N-, or O-atoms. In cases of slow exchange the isotope shifts were obtained from solutions containing both isotopomers, whereas for fast exchange (acidic solutions) either separate NMR. sample tubes

  已经研究了氘对烯胺酮的13 C和15 N化学位移的影响。据报道中性和质子化物种的D / H同位素位移，即当同位素在C（2）-，N-或O原子上交换时。在交换缓慢的情况下，同位素位移是从同时包含两种同位素异构体的溶液中获得的，而对于快速交换（酸性溶液），则需要单独的NMR。使用样品管（15 N-NMR。）或同轴管（13 C-NMR。）。
• 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。
• Photoinduced Three‐Component Cyclization of Arylamines, Enaminones and Difluorobromoacetates to 2,3‐Difunctionalized Quinolines
  作者：Jie Huo、Xiao Geng、Wanmei Li、Pengfei Zhang、Lei Wang

  DOI：10.1002/adsc.202200615

  日期：2022.10.18

  A photoinduced multicomponent reaction of arylamines, enaminones and difluorobromoacetates for the synthesis of 2,3-difunctionalized quinolines is reported. This strategy features broad functional groups tolerance and wide substrate scopes that enables further synthetic applications of the obtained products. Mechanistic studies reveal that intermolecular [3+3] cyclization between in-situ generated

  报道了芳胺、烯胺酮和二氟溴乙酸酯的光诱导多组分反应，用于合成 2,3-双官能化喹啉。该策略具有广泛的官能团耐受性和广泛的底物范围，可以进一步合成应用所获得的产品。机理研究表明，原位产生的1,3-乙烯基亚胺离子和芳胺之间的分子间[3+3]环化是这一转变的关键步骤。