cis-2-methyl-4-(iodomethyl)-γ-butyrolactone | 1729-31-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: cis-2-methyl-4-(iodomethyl)-γ-butyrolactone
• 英文别名: cis-2-methyl-4-iodomethyl-γ-butyrolactone；cis-3-methyl-5-iodomethyl-4,5-dihydrofuran-2-one；cis-5-Iod-2-methyl-4-pentanolid；(3S,5S)-5-(iodomethyl)-3-methyloxolan-2-one
• CAS: 1729-31-3；88431-10-1；88431-20-3；110658-34-9；115362-50-0；131175-59-2；131232-35-4
• 化学式: C₆H₉IO₂
• 分子量: 240.041
• InChiKey: FRFKYMPKNNZPTP-WHFBIAKZSA-N

物化性质

• 沸点：
  310.8±15.0 °C(Predicted)
• 密度：
  1.763±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  (S)-1-(2-(hydroxymethyl)pyrrolidin-1-yl)pent-4-en-1-one 在 水 、 碘 、 lithium diisopropyl amide 作用下， 以 乙二醇二甲醚 为溶剂， 反应 72.0h， 生成 cis-2-methyl-4-(iodomethyl)-γ-butyrolactone
  参考文献：
  名称：

  Enantioselective route to .gamma.-butyrolactones: chiral auxiliary mediated amide alkylation and iodolactonization

  摘要：

  A number of chiral, gamma, delta-unsaturated amides (1 and 2) have been prepared and their subsequent alkylation and iodolactonization to gamma-butyrolactones (3) investigated.

  DOI：

  10.1021/jo00313a005

文献信息

• An efficient route to 1,3-amino hydroxyl system via electrophilic lactonization of 2-amino-4-pentenoic acid derivatives. Stereoselective synthesis of (−)-bulgecinine
  作者：Yasufumi Ohfune、Keiko Hori、Masahiro Sakaitani

  DOI：10.1016/s0040-4039(00)85403-9

  日期：1986.1

  Several γ-hydroxy-α-amino acid systems were prepared stereoselectively from 2-amino-4-pentenoic acid derivatives using electrophilic lactonization. This strategy was applied to the synthesis of a highly functionalized proline analogue, (−)-bulgecinine (4).

  使用亲电子内酯化作用，由2-氨基-4-戊烯酸衍生物立体选择性地制备了几种γ-羟基-α-氨基酸系统。该策略被用于合成高度功能化的脯氨酸类似物（-）-bulgecinine（4）。
• 1,3-Asymmetric induction: highly stereoselective synthesis of 2,4-trans-disubstituted γ-butyrolactones and γ-butyrothiolactones
  作者：Yoshinao Tamaru、Masato Mizutani、Yutaka Furukawa、Shinichi Kawamura、Zenichi Yoshida、Kazunori Yanagi、Masao Minobe

  DOI：10.1021/ja00316a044

  日期：1984.2

  Etude de l'induction asymetrique trans-1,3 au cours de l'halogenolactonisation des dimethylamides des acides α-methyl- ou α-benzyl alcene-4oiques ou alcene-4thioiques conduisant aux perhydrofurannones-2 et -thiophenones-2 trans-disubstituees-3,5 (les acides α,β-disubstitues conduisent aux (thio) lactones trisubstituees-3,4,5)

  Etude de l'induction asymetrique trans-1,3 au cours de l'halogenolactonisation des dimethylamides des acides α-methyl-ou α-benzyl alcene-4oiques ou alcene-4thioiques conduisant aux perhydrofurannones-2 et-thiophenones-2 trans-disubstitu 3,5 (les acides α,β-disubstitues conduisent aux (thio)lactones trisubstituees-3,4,5)
• Guenther, Hans Juergen; Guntrum, Eberhard; Jaeger, Volker, Liebigs Annalen der Chemie, 1984, # 1, p. 15 - 30
  作者：Guenther, Hans Juergen、Guntrum, Eberhard、Jaeger, Volker

  DOI：——

  日期：——
• Preparation of Nonracemic 3,5-Disubstituted-.gamma.-butyrolactones: An Effective Sequent Auxiliary for Amide Alkylation and Iodolactonization
  作者：Hongsik Moon、Shawn W. E. Eisenberg、Mark E. Wilson、Neil E. Schore、Mark J. Kurth

  DOI：10.1021/jo00101a002

  日期：1994.11

  The effective dual use of a chiral auxiliary in two sequential steps is reported; this sequent auxiliary mediates diastereoselective C-C bond formation in the first step and mediates diastereoselective heterocyclization in the second step.
• Iodobenzene-catalysed iodolactonisation using sodium perborate monohydrate as oxidant
  作者：Hongjun Liu、Choon-Hong Tan

  DOI：10.1016/j.tetlet.2007.09.078

  日期：2007.11

  A convenient approach has been developed for iodolactonisation using iodobenzene as catalyst. The active reagent was generated in situ with tetra-n-butylammonium iodide (TBAI) and hypervalent iodine reagent, diacetoxyiodobenzene (PIDA). PIDA, in turn, was generated in situ using a catalytic amount of iodobenzene with sodium perborate monohydrate as the stoichiometric oxidant. A variety of olefinic acids including delta-pentenoic acids, delta-pentynoic acids and delta-hexynoic acid gave high yields of lactones using this methodology. (C) 2007 Elsevier Ltd. All rights reserved.