3,4-bismethylene-1,6-hexanediol | 172985-52-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3,4-bismethylene-1,6-hexanediol
• 英文别名: 3,4-dimethylenehexane-1,6-diol；3,4-Bis(methylene)hexane-1,6-diol；3,4-dimethylidenehexane-1,6-diol
• CAS: 172985-52-3
• 化学式: C₈H₁₄O₂
• 分子量: 142.198
• InChiKey: KPFMKULCYCMGKG-UHFFFAOYSA-N

物化性质

• 沸点：
  287.3±20.0 °C(Predicted)
• 密度：
  0.978±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3,4-bismethylene-1,6-hexanediol 在 吡啶 、 potassium tert-butylate 、 potassium carbonate 作用下， 以 二甲基亚砜 、 苯 为溶剂， 反应 43.5h， 生成 1,1-dichloro-9-methylene-6-azaspiro[2,6]non-6-yl-p-tolylsulfone
  参考文献：
  名称：

  8,11-Dichloro-N-tosyl-3-aza[5]metacyclophane:  A Highly Strained Aromatic System

  摘要：

  DOI：

  10.1021/ja9634987
• 作为产物：
  描述：

  diethyl 3,4-dimethylenehexanedioate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以80%的产率得到3,4-bismethylene-1,6-hexanediol
  参考文献：
  名称：

  合成有机光化学中的反应控制：环加成的[5 + 2]和[2 + 2]模式之间的切换

  摘要：

  人格分裂：已开发出能够有效控制马来酰亚胺中光环加成模式的反应条件。直接辐射有利于[5 + 2]模式，而敏化辐射则允许完全切换到[2 + 2]模式（请参阅方案； TBS =叔丁基二甲基甲硅烷基）。

  DOI：

  10.1002/anie.200904059

文献信息

• Copper-Catalyzed Dehydrogenative Diels–Alder Reaction
  作者：Bing Jiang、Qiu-Ju Liang、Yu Han、Meng Zhao、Yun-He Xu、Teck-Peng Loh

  DOI：10.1021/acs.orglett.8b01067

  日期：2018.6.1

  A practical and effective copper-catalyzed dehydrogenative Diels–Alder reaction of gem-diesters and ketone with dienes has been established. The active dienophiles were generated in situ via a radical-based dehydrogenation process, which reacted with a wide variety of dienes to afford various polysubstituted cyclohexene derivatives in good to excellent yields.

  的实用而有效的铜催化脱氢Diels-Alder反应宝石-diesters和与二烯烃酮已经建立。通过基于自由基的脱氢过程原位产生活性二烯亲和体，其与多种二烯反应，以良好或优异的收率得到各种多取代的环己烯衍生物。
• Reaction Control in Synthetic Organic Photochemistry: Switching between [5+2] and [2+2] Modes of Cycloaddition
  作者：Claudio Roscini、Kara L. Cubbage、Malcolm Berry、Andrew J. Orr-Ewing、Kevin I. Booker-Milburn

  DOI：10.1002/anie.200904059

  日期：2009.11.2

  Split personality: Reaction conditions that enable powerful control over the mode of photocycloaddition in maleimides have been developed. Direct irradiation favors the [5+2] mode whereas sensitized irradiation allows a complete switch to the [2+2] mode (see scheme; TBS=tert‐butyldimethylsilyl).

  人格分裂：已开发出能够有效控制马来酰亚胺中光环加成模式的反应条件。直接辐射有利于[5 + 2]模式，而敏化辐射则允许完全切换到[2 + 2]模式（请参阅方案； TBS =叔丁基二甲基甲硅烷基）。
• Synthesis of constrained α-amino acid derivatives via Diels-Alder approach
  作者：Sambasivarao Kotha、Enugurthi Brahmachary、Nampally Sreenivasachary

  DOI：10.1016/s0040-4039(98)00562-0

  日期：1998.6

  Synthesis of new five and seven membered outer ring diene building blocks containing alpha-amino acid moiety and their usage in the preparation of the constrained amino acid derivatives is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of benzocycloheptene-based amino acid derivatives via a [4+2] cycloaddition reaction as a key step
  作者：Sambasivarao Kotha、Nampally Sreenivasachary、Enugurthi Brahmachary

  DOI：10.1016/s0040-4020(01)00575-0

  日期：2001.7

  The seven-membered diene 5 is prepared from 2-butyne-1,4-diol using double orthoester Claisen rearrangement reaction as a key step. The Diels-Alder reaction of the diene 5 with various dienophiles followed by oxidation delivered the benzocycloheptene-based a-amino acid derivatives in very good yields. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Synthesis of 2,6-dioxabicyclo[3.3.0]octanes and 3,8-dioxabicyclo[4.4.0]dec-1(6)-enes by electrophilic cyclization of 3,4-dimethylene-1,6-hexanediols
  作者：M. E. Gurskii、S. B. Golovin、M. O. Dekaprilevich、Yu. T. Struchkov、Yu. N. Bubnov

  DOI：10.1007/bf00700900

  日期：1995.7

  3,4-Dimethylene-1,6-hexane diols 2 obtained by allylboration of ketones with 2,3-dimethylene-1,4-bis(dipropylboryl)butane 1 undergo cyclization on treatment with I-2/NaHCO3 to give 1,5-cis-di(iodomethyl)-2,6-dioxabicyclo[3.3.0]octanes (4) and/or 3,8-dioxabicyclo[4.4.0]dec-1(6)-enes (5). 4,4,9,9-Tetramethyl-3,8-dioxacyclodeca-1,6-dione (9) was synthesized by ozonolysis of bicyclic compound 5b. The structure of compound 5e was confirmed by X-ray diffraction analysis.

表征谱图