trans-2-(benzyl)-4-(iodomethyl)-γ-butyrolactone

• 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: trans-2-(benzyl)-4-(iodomethyl)-γ-butyrolactone
• 英文别名: (3R,5S)-3-benzyl-5-(iodomethyl)oxolan-2-one
• 化学式: C₁₂H₁₃IO₂
• 分子量: 316.139
• InChiKey: CKQGFWUXIGENQK-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  N,N-dimethyl-2-benzyl-4-pentenamide 在 碘 作用下， 以 乙二醇二甲醚 、 水 为溶剂， 反应 96.0h， 生成 trans-2-(benzyl)-4-(iodomethyl)-γ-butyrolactone 、 cis-2-(benzyl)-4-(iodomethyl)-γ-butyrolactone
  参考文献：
  名称：

  1,3-不对称诱导：2,4-反式二取代γ-丁内酯和γ-丁硫内酯的高度立体选择性合成

  摘要：

  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)

  DOI：

  10.1021/ja00316a044

文献信息

• The Chiral Auxiliary <i>N</i>-1-(1′-Naphthyl)ethyl-<i>O</i>-<i>tert</i>-butylhydroxylamine: A Chiral Weinreb Amide Equivalent
  作者：Alexander N. Chernega、Stephen G. Davies、Christopher J. Goodwin、David Hepworth、Wataru Kurosawa、Paul M. Roberts、James E. Thomson

  DOI：10.1021/ol901174t

  日期：2009.8.6

  The chiral auxiliary N-1-(1'-naphthyl)ethyl-O-tert-butylhydroxylamine is readily prepared from N-hydroxyphthalimide in four steps, with resolution giving access to both enantiomers in >98% ee, on a multigram (>25 g) scale. Conversion to a range of N-acyl derivatives, followed by highly diastereoselective alkylation (>= 94% de) gives the corresponding chiral, 2-substituted derivatives as single diastereoisomers (>98% de) after chromatography. Reductive cleavage with LlAlH(4) allows direct access to chiral aldehydes, and treatment with MeLi gives chiral methyl ketones in excellent enantiopurity (>= 94% ee). The auxiliary can be recovered in >98% ee and recycled.
• 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.
• Solid-Phase Organic Synthesis of 5-Iodomethyl-dihydrofuran-2-ones with Recyclable Polymer-Supported Selenium Bromide
  作者：Chao-Li Wang、Shou-Ri Sheng、Xin Cheng、Ming-Zhong Cai

  DOI：10.1080/00397911.2010.524064

  日期：2012.2.1

  Reaction of polystyrene-supported selenium bromide with gamma,delta-unsaturated acids and subsequent cleavage from the polymer by treatment with methyl iodide efficiently afforded 5-iodomethyl-dihydrofuran-2-ones in excellent yields. The polymeric reagent can be regenerated and reused as an environmentally friendly reagent.
• TAMARU, YOSHINAO;MIZUTANI, MASATO;FURUKAWA, YUTAKA;KAWAMURA, SHIN-ICHI;YO+, J. AMER. CHEM. SOC., 1984, 106, N 4, 1079-1085
  作者：TAMARU, YOSHINAO、MIZUTANI, MASATO、FURUKAWA, YUTAKA、KAWAMURA, SHIN-ICHI、YO+

  DOI：——

  日期：——
• 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)