Allyl 2-undecynoate | 155529-53-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: Allyl 2-undecynoate
• 英文别名: Prop-2-enyl undec-2-ynoate
• CAS: 155529-53-6
• 化学式: C₁₄H₂₂O₂
• 分子量: 222.327
• InChiKey: RZQDVIPUQLNWGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  16
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  Allyl 2-undecynoate 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex lithium bromide 、 copper(ll) bromide 作用下， 以 溶剂黄146 为溶剂， 反应 10.0h， 以81%的产率得到α-(Z)-(1'-Bromononylidene)-β-(bromomethyl)-γ-butyrolactone
  参考文献：
  名称：

  Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications

  摘要：

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.

  DOI：

  10.1021/jo00110a018
• 作为产物：
  描述：

  十一碳-2-炔酸 、 3-溴丙烯 在 sodium carbonate 作用下， 以 六甲基磷酰三胺 为溶剂， 以95%的产率得到Allyl 2-undecynoate
  参考文献：
  名称：

  Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications

  摘要：

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.

  DOI：

  10.1021/jo00110a018

文献信息

• Selective ene-yne coupling-functionalization: A new strategy in constructing heterocycles
  作者：Zhong Wang、Xiyan Lu

  DOI：10.1016/0040-4020(95)00035-7

  日期：1995.2

  Fluorinated derivatives of 3-alkylidene-2(3H)-dihydrofuranone have been synthesized by sodium dithionite initiated tandem perfluoroalkylation-cyclization of allylic 2-alkynoates in fair to good yield and high stereoselectivity. Fluorinated 3-alkylidene-2(3H)-pyrrolidone derivatives were prepared similarly. A mechanistic rationale concerning the different radical steps and the differences between esters

  通过连二亚硫酸钠引发的烯丙基2-链烷酸酯的串联全氟烷基化-环化反应合成了3-亚烷基-2（3H）-二氢呋喃酮的氟化衍生物，其收率相当好且具有高立体选择性。类似地制备氟化的3-亚烷基-2（3H）-吡咯烷酮衍生物。给出了关于不同的自由基步骤以及酯和酰胺之间的差异的机械原理。
• Palladium catalyzed cyclization-carbonylation of allylic 2-alkynoates: Facile synthesis of α-alkylidene-γ-butyrolactone β-acetic acid derivatives
  作者：Jianguo Ji、Xiyan Lu

  DOI：10.1016/s0040-4020(01)85373-4

  日期：1994.1

  alpha-(Z)- and (E)- Chtoroalkylidene-gamma-butyrolactone beta-acetic acid derivatives were prepared from easily available acyclic allylic 2-alkynoates using Pd-2(dba)(3) CHCl3 as catalyst under 1 atm of CO in the presence of CuCl2 and LiCl in high stereoselectivity.
• A convenient stereoselective synthesis of fluorinated α-alkylidene-γ-butyrolactone derivatives
  作者：Xiyan Lu、Zhong Wang、Jianguo Ji

  DOI：10.1016/s0040-4039(00)75852-7

  日期：1994.1

  Fluorinated alpha-alkylidene-gamma-butyrolactone derivatives were synthesized stereoselectively via a sodium dithionite initiated radical perfluoroalkylation-cyclization of acyclic allylic alkynoates in high yields under mild conditions.
• Lu Xiyan, Wang Zhong, Ji Jianguo, Tetrahedron Lett, 35 (1994) N 4, S 613-616
  作者：Lu Xiyan, Wang Zhong, Ji Jianguo

  DOI：——

  日期：——
• Palladium-Templated Regio- and Stereoselective Cyclization of 2'-Alkenyl 2-Alkynoates and Its Synthetic Applications
  作者：Jianguo Ji、Chunming Zhang、Xiyan Lu

  DOI：10.1021/jo00110a018

  日期：1995.3

  2'-Alkenyl 2-alkynoates undergo facile stereoselective cyclization to alpha-(haloalkylidene)-gamma-butyrolactones upon treatment with a catalytic amount of palladium complex in the presence of CuX(2) and LiX. When an alkyl group is introduced to the 1'-position of the alkenyl group, unsubstituted 2-propynoates mainly give trans-beta, gamma-disubstituted gamma-lactones, and substituted 2-propynoates afford cis-beta,gamma-disubstituted gamma-lactones. Further elaborations of the halogen atoms and the synthesis of A-factor using this method are exemplified.