(2Z,4E)-ethyl 2-bromo-6-phenylpenta-2,4-dienoate | 197313-84-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2Z,4E)-ethyl 2-bromo-6-phenylpenta-2,4-dienoate
• 英文别名: ethyl (2Z,4E)-2-bromo-5-phenylpenta-2,4-dienoate；ethyl 2-bromo-5-phenylpenta-2,4-dienoate；(2Z,4E)-ethyl 2-bromo-5-phenylpenta-2,4-dienoate
• CAS: 197313-84-1
• 化学式: C₁₃H₁₃BrO₂
• 分子量: 281.149
• InChiKey: GBWHSKURMDEJBC-QJUYYABZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  (2Z,4E)-ethyl 2-bromo-6-phenylpenta-2,4-dienoate 在 AD-mix-α 、 tin(ll) chloride 作用下， 生成 ethyl (Z)-2-bromo-3-[(4S,5S)-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-yl]prop-2-enoate
  参考文献：
  名称：

  Synthesis and reactions of chiral 5-substituted (Z)-ethyl 2-bromo-3-(1,3-dioxolan-4-yl)-2-propenoates

  摘要：

  Wittig olefination of the aldehydes 2a/b gave the 2-bromo-dienes 3a/b. Regioselective catalytic Sharpless asymmetric dihydroxylation (AD) led to the diols 4a/b with high enantiomeric excess (ee > 94%). Cascade reactions of 5a/b with dienolate 6 yielded 7a/b with excellent diastereomeric excess(de > 95%). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01648-1
• 作为产物：
  描述：

  反式肉桂醛 、 ethyl 2-bromo-2-(triphenylphosphoranylidene)acetate 生成 (2Z,4E)-ethyl 2-bromo-6-phenylpenta-2,4-dienoate
  参考文献：
  名称：

  Synthesis and reactions of chiral 5-substituted (Z)-ethyl 2-bromo-3-(1,3-dioxolan-4-yl)-2-propenoates

  摘要：

  Wittig olefination of the aldehydes 2a/b gave the 2-bromo-dienes 3a/b. Regioselective catalytic Sharpless asymmetric dihydroxylation (AD) led to the diols 4a/b with high enantiomeric excess (ee > 94%). Cascade reactions of 5a/b with dienolate 6 yielded 7a/b with excellent diastereomeric excess(de > 95%). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)01648-1

文献信息

• A new route to α-trifluoromethyl-α,β-unsaturated esters
  作者：Xingang Zhang、Feng-Ling Qing、Yonggang Yang、Jiang Yu、Xiang-Kai Fu

  DOI：10.1016/s0040-4039(00)00279-3

  日期：2000.4

  The treatment of α-bromo-α,β-unsaturated esters with FSO2CF2CO2Me and CuI in DMF/HMPA constitutes a new synthetic scheme for the preparation of α-trifluoromethyl-α,β-unsaturated esters.

  在DMF / HMPA中用FSO 2 CF 2 CO 2 Me和CuI处理α-溴-α，β-不饱和酯构成了制备α-三氟甲基-α，β-不饱和酯的新合成方案。
• One-Pot Combination of the Wittig Olefination with Bromination and Oxidation Reactions
  作者：Usama Karama、Refat Mahfouz、Zeid Al-Othman、Ismail Warad、Abdulrahman Almansour

  DOI：10.1080/00397911.2011.614712

  日期：2013.2.1

  Abstract A simple one-pot process for in situ bromination of (ethoxycarbonylmethylene)-triphenylphosphorane 1 was carried out. This was followed by oxidation of alcohol using SO3. Pyridine complex as a mild oxidant and in situ trapping of the aldehyde. This process constitutes a stereoselective one-pot procedure for the preparation of Z-configured α-bromo-α, β-unsaturated esters in good yield. GRAPHICAL

  摘要 进行了（乙氧基羰基亚甲基）-三苯基正膦 1 原位溴化的简单一锅法。然后使用 SO3 氧化醇。吡啶络合物作为温和的氧化剂并原位捕获醛。该方法构成了一种立体选择性的一锅法，用于以良好的收率制备 Z-构型的 α-溴-α，β-不饱和酯。图形概要
• Chemoselective Construction of Substituted Conjugated Dienes Using an Olefin Cross-Metathesis Protocol
  作者：Timothy W. Funk、Jon Efskind、Robert H. Grubbs

  DOI：10.1021/ol047929z

  日期：2005.1.1

  [Reaction: see text] Various substituted conjugated dienes have been made by olefin cross-metathesis. Using either electronic or steric "protection," one of the olefins of the conjugated diene was deactivated relative to the other for cross-metathesis. The reactions proceed with very high chemoselectivity and, when steric deactivation is used, very high diastereoselectivity.

  [反应：见正文]通过烯烃交叉复分解制备了各种取代的共轭二烯。使用电子或空间“保护”，使共轭二烯的一种烯烃相对于另一种失活以进行交叉复分解。反应以非常高的化学选择性进行，并且当使用空间减活时，非常高的非对映选择性。
• A Facile One-Pot Synthesis of α-Bromo-α,β-unsaturated Esters from Alcohols
  作者：Usama Karama、Zeid Al-Othman、Abdullah Al-Majid、Abdulrahman Almansour

  DOI：10.3390/molecules15053276

  日期：——

  in CH2Cl2 followed by the addition of an alcohol in the presence of manganese dioxide under ultrasonic irradiation constitutes a stereoselective one-pot procedure for the preparation of Z-configured α–bromo-α,β-unsaturated esters in good to excellent yield.

  在 CH2Cl2 中用（碳乙氧基亚甲基）三苯基正膦（1）处理 N-溴代琥珀酰亚胺（NBS），然后在二氧化锰的存在下在超声波照射下加入醇，构成了一种立体选择性的一锅法制备 Z-构型的 α-溴-α,β-不饱和酯的产率非常好。
• Chemoselective Bromination of Dienoates
  作者：Valentina A. Kobelevskaya、Alexander V. Popov、Sergey V. Zinchenko、Alexander Yu. Rulev

  DOI：10.1002/ejoc.202000893

  日期：2020.9.14

  One isomer or another! Chemo‐ and stereoselectivity of dienoates bromination depends strongly on the substituent nature in starting ester and reaction conditions.

  一个异构体或另一个！二烯酸酯溴化的化学和立体选择性在很大程度上取决于起始酯和反应条件下的取代基性质。