methyl (2Z)-3-hydroxy-2-(iodomethylidene)-4-methylpentanoate | 178173-68-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: methyl (2Z)-3-hydroxy-2-(iodomethylidene)-4-methylpentanoate
• CAS: 178173-68-7
• 化学式: C₈H₁₃IO₃
• 分子量: 284.094
• InChiKey: CCDRQUJALLVPDX-XQRVVYSFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  12
• 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：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2Z)-3-hydroxy-2-(iodomethylidene)-4-methylpentanoate 在 lithium hydroxide 、 Petasis 、 甲基磺酰氯 作用下， 以 甲苯 为溶剂， 生成 2-isopropyl-3-iodomethylene-4-methyleneoxetane
  参考文献：
  名称：

  Unusual, Strained Heterocycles:  3-Alkylidene-2-methyleneoxetanes from Morita−Baylis−Hillman-type Adducts

  摘要：

  [GRAPHICS]3-Alkylidene-2-methyleneoxetanes have been prepared by treating alpha-alkylidene-beta-lactones, derived from Morita-Baylis-Hillman-type adducts, with dimethyltitanocene. Preliminary studies of the reactivity of these little known, strained heterocycles are also described.

  DOI：

  10.1021/ol020202v
• 作为产物：
  描述：

  异丁醛 、 丙炔酸甲酯 在 氯化锆(IV) 、 四丁基碘化铵 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 生成 3-Hydroxy-2-[1-iodo-meth-(E)-ylidene]-4-methyl-pentanoic acid methyl ester 、 methyl (2Z)-3-hydroxy-2-(iodomethylidene)-4-methylpentanoate
  参考文献：
  名称：

  Stereoselective Synthesis of Methyl (Z)-3-Iodo-2-(1-hydroxyalkyl)prop-2-enoates and Their Further Transformation to α-(Z)-Iodomethylene-β-lactones

  摘要：

  甲基丙炔酸酯、碘离子与醛或酮在ZrCl4催化剂的存在下进行串联亲核加成-醇醛反应，获得了高Z选择性的甲基3-碘-2-(1-羟基烷基)丙-2-烯酸酯，这些产物进一步转化为良好产率的α-(Z)-碘甲烯-β-内酯。

  DOI：

  10.1055/s-1996-4266

文献信息

• [EN] NOVEL BETA SUBSTITUTED MORITA-BAYLIS-HILLMAN DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS DE LA RÉACTION DE MORITA-BAYLIS-HILLMAN À SUBSTITUTION BÊTA
  申请人：UNIV SUNGKYUNKWAN FOUND

  公开号：WO2009110655A1

  公开（公告）日：2009-09-11

  Provided are β-substituted Morita-Baylis-Hillman (MBH) derivatives, pharmaceutically acceptable salts, hydrates, solvates and stereoisomers thereof. The derivatives may be prepared by preparing β-iodo-MBH esters from a variety of carbonyl compounds such as aldehydes and ketones, or imines in the presence of a Lewis acid as a basic backbone, and substituting iodide on a vinyl position with a variety of substituents. In addition, the β-substituted MBH derivatives have an excellent pharmaceutical effect in preventing and treating cancer.

  提供了β-取代的Morita-Baylis-Hillman（MBH）衍生物，其药用盐、水合物、溶剂合物和立体异构体。这些衍生物可以通过从各种羰基化合物（如醛和酮）或亚胺制备β-碘代MBH酯来制备，或者在存在路易斯酸作为基础骨架的情况下，用各种取代基替换乙烯位的碘化物。此外，β-取代的MBH衍生物在预防和治疗癌症方面具有出色的药效。
• A Stereoselective Synthesis of α-(1-Hydroxyalkyl)-β-Substituted Acrylic Acid Esters
  作者：Taı̈cir Ben Ayed、Jean Villiéras、Hassen Amri

  DOI：10.1016/s0040-4020(99)01079-0

  日期：2000.1
• Unusual, Strained Heterocycles:  3-Alkylidene-2-methyleneoxetanes from Morita−Baylis−Hillman-type Adducts
  作者：Isamir Martínez、Alexander E. Andrews、Joseph D. Emch、Albert J. Ndakala、Jun Wang、Amy R. Howell

  DOI：10.1021/ol020202v

  日期：2003.2.1

  [GRAPHICS]3-Alkylidene-2-methyleneoxetanes have been prepared by treating alpha-alkylidene-beta-lactones, derived from Morita-Baylis-Hillman-type adducts, with dimethyltitanocene. Preliminary studies of the reactivity of these little known, strained heterocycles are also described.
• Stereoselective Synthesis of Methyl (Z)-3-Iodo-2-(1-hydroxyalkyl)prop-2-enoates and Their Further Transformation to α-(Z)-Iodomethylene-β-lactones
  作者：Chunming Zhang、Xiyan Lu

  DOI：10.1055/s-1996-4266

  日期：1996.5

  The tandem nucleophilic addition-aldol reaction of methyl propynoate, iodide ion, and aldehydes or ketones in the presence of ZrCl4 as the catalyst gave methyl 3-iodo-2-(1-hydroxyalkyl)prop-2-enoates with high Z selectivity, which were further transformed to α-(Z)-iodomethylene-β-lactones in good yield.

  甲基丙炔酸酯、碘离子与醛或酮在ZrCl4催化剂的存在下进行串联亲核加成-醇醛反应，获得了高Z选择性的甲基3-碘-2-(1-羟基烷基)丙-2-烯酸酯，这些产物进一步转化为良好产率的α-(Z)-碘甲烯-β-内酯。