methyl (Z)-11-bromo-1-undecenoate | 182816-00-8

• 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: methyl (Z)-11-bromo-1-undecenoate
• 英文别名: methyl (Z)-11-bromo-10-undecenoate；methyl (Z)-11-bromoundec-10-enoate
• CAS: 182816-00-8
• 化学式: C₁₂H₂₁BrO₂
• 分子量: 277.202
• InChiKey: BMFLKLDETCMSPJ-LUAWRHEFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  methyl (E)-10-carbomethoxy-1-decenylboronic acid 在 N-氯代丁二酰亚胺 、 sodium bromide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以76%的产率得到methyl (Z)-11-bromo-1-undecenoate
  参考文献：
  名称：

  Kabalka, George W.; Sastry, Kunda A. R.; Knapp, Furn, F., Synthetic Communications, 1983, vol. 13, # 12, p. 1027 - 1032

  摘要：

  DOI：

文献信息

• A general and convenient synthetic method of geometrically pure (Z)-1-bromo-1-alkenes
  作者：Jun'ichi Uenishi、Reiko Kawahama、Yasuhiko Shiga、Osamu Yonemitsu、Jiro Tsuji

  DOI：10.1016/s0040-4039(96)01461-x

  日期：1996.9

  Palladium catalyzed hydrogenolysis of 1,1-dibromo-1-alkenes by tributyltin hydride proceeds smoothly to give (Z)-1-bromo-1-alkenes with excellent stereoselectivity in good yields. Dibromomethylenation of aldehydes by a combination of CBr4 and Ph3P in methylene chloride and the successive hydrogenolysis affords (Z)-1-bromo-1-alkenes in one-pot.

  氢化三丁基锡对钯催化的1,1-二溴-1-烯烃的氢解反应进行得很顺利，从而以良好的收率获得了具有出色立体选择性的（Z）-1-溴-1-烯烃。通过在二氯甲烷中将CBr 4和Ph 3 P组合进行醛的二溴甲基化，然后连续进行氢解，一锅得到（Z）-1-溴-1-烯烃。
• Stereoselective Hydrogenolysis of 1,1-Dibromo-1-alkenes and Stereospecific Synthesis of Conjugated (<i>Z</i>)-Alkenyl Compounds
  作者：Jun'ichi Uenishi、Reiko Kawahama、Osamu Yonemitsu、Jiro Tsuji

  DOI：10.1021/jo9812781

  日期：1998.11.1

  The Pd-catalyzed hydrogenolysis of 1,1-dibromoalkenes with Bu3SnH occurs at room temperature stereoselectively to give (Z)-1-bromo-1-alkenes. We sought to determine the optimal reaction conditions and illustrate the scope of this method with 32 dibromoalkenes including alkenyl- and alkynyl-conjugated 1,l-dibromo-l-alkenes 7a-h and 2,2-disubstituted I,1-dibromo-1-alkenes 9a-f. Triphenylphosphine was the best ligand for the Pd-catalyzed hydrogenolysis. A wide range of solvents can be used for this reaction excluding EtOH, AcOH, and CHCl3. However, the reaction proceeds even in these solvents with the addition of a cosolvent or radical scavenger. The reaction of 1,1-diiodo-1-alkene (3) gave a mixture of (Z)-1-iodo-1-alkene (4), (Z)-1-tributylstannyl-1-alkene (5), and a terminal alkene 6, while that of 1,1-dichloroalkene did not occur. This selectivity can be explained by the stereoselective insertion of Pd(0) to a trans bromine-alkenyl carbon bond, successive transmetalation with Bu3SnH, and reductive elimination. The Suzuki and Sonogashira couplings of the resulting (Z)-1-bromo-1-alkenes with alkenyl(dialkoxy)borane and terminal alkyne occurred to give conjugated polyenes and enynes stereospecifically. The Pd-catalyzed hydrogenolysis of 1,l-dibromo-l-alkene and successive cross-coupling can be carried out either in a stepwise manner or in one-pot under the same Pd catalysis. These two processes should be useful for the synthesis of geometrically pure polyene and enyne with a Z-alkenyl unit.
• KABALKA, G. W.;SASTRY, KUNDA, A. R.;KNAPP, FURN, F.;SRIVASTAVA, PREM, C., SYNTH. COMMUN., 1983, N 12, 1027-1032
  作者：KABALKA, G. W.、SASTRY, KUNDA, A. R.、KNAPP, FURN, F.、SRIVASTAVA, PREM, C.

  DOI：——

  日期：——
• Kabalka, George W.; Sastry, Kunda A. R.; Knapp, Furn, F., Synthetic Communications, 1983, vol. 13, # 12, p. 1027 - 1032
  作者：Kabalka, George W.、Sastry, Kunda A. R.、Knapp, Furn, F.、Srivastava, Prem C.

  DOI：——

  日期：——