Methanesulfonic acid (Z)-3-iodo-but-2-enyl ester | 167385-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (Z)-3-iodo-but-2-enyl ester
• CAS: 167385-39-9
• 化学式: C₅H₉IO₃S
• 分子量: 276.095
• InChiKey: JJLRMEVPCSAZFD-HYXAFXHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (Z)-3-iodo-but-2-enyl ester 在 lithium bromide 作用下， 以 丙酮 为溶剂， 反应 0.42h， 生成 2-丁烯,1-溴-3-碘-,(2Z)-
  参考文献：
  名称：

  Studies Directed toward the Total Synthesis of Cerorubenic Acid-III. 4. Exploration of an Organometallic Approach to Construction of the Eastern Sector

  摘要：

  The concept of an intramolecular organometallic approach to the most illustrious member of the cerorubenic acid family is outlined. Alkylation of ketone 2 with the ethyl iodoacetate and conversion of the resultant intermediate into lactone 9 provided a ready means for attaching side chains carrying a vinyl iodide substituent. Arrival at the key iodo ketones was next realized by a three-step sequence involving sodium borohydride reduction, regiocontrolled silylation of the primary hydroxyl group in the diol, and Dess-Martin oxidation. The crucial six-membered cyclization of these intermediates is not favored kinetically, and reductive deiodination was observed, if reaction occurred at all. Attempts to generate vinyl stannanes from these same substrates were also ineffective. The failure of this approach demonstrates the difficulties associated with closure of ring D, a phenomenon that has earlier been observed in the context of other exploratory routes to cerorubenic acid-III.

  DOI：

  10.1021/jo00120a026
• 作为产物：
  描述：

  3-iodo-but-2-ene-1-ol 、 甲基磺酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 Methanesulfonic acid (Z)-3-iodo-but-2-enyl ester
  参考文献：
  名称：

  不对称的heck反应阴离子捕获过程。Capnellenols关键中间体的催化不对称合成

  摘要：

  通过不对称的Heck反应和随后的乙酸根阴离子捕获过程，实现了萘酚的关键中间体4和15的催化不对称合成。此外，上述反应已成功地用于不对称的Heck反应-胺捕获过程。

  DOI：

  10.1016/s0040-4020(01)80534-2

文献信息

• Stereocontrolled synthesis of (S)-9-cis-4-oxo-13,14-dihydroretinoic acid
  作者：Marta Domínguez、Susana Álvarez、Rosana Álvarez、Ángel R. de Lera

  DOI：10.1016/j.tet.2011.12.056

  日期：2012.2

  (S)-9-cis-4-Oxo-13,14-dihydroretinoic acid (S)-1, a new major endogenous vitamin A metabolite that activates retinoic acid receptor signaling both in vitro and in vivo, has been synthesized stereoselectively by Horner-Wadsworth-Emmons condensation and Stille cross-coupling as bond forming reactions. (C) 2011 Elsevier Ltd. All rights reserved.