1-bromo-1-chloro-4,4-dimethylpentyne-2 | 138777-53-4

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机氯化物
• 英文名称: 1-bromo-1-chloro-4,4-dimethylpentyne-2
• 英文别名: 1-Bromo-1-chloro-4,4-dimethylpent-2-yne
• CAS: 138777-53-4
• 化学式: C₇H₁₀BrCl
• 分子量: 209.513
• InChiKey: YLTOAEPVCJMSBQ-UHFFFAOYSA-N

物化性质

• 沸点：
  197.8±25.0 °C(Predicted)
• 密度：
  1.374±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  2,3-二甲基-2-丁烯 、 1-bromo-1-chloro-4,4-dimethylpentyne-2 在 potassium tert-butylate 作用下， 以 正戊烷 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  Alkynylhalocarbenes 1. Generation of alkynylchloro- and alkynylbromocarbenes from alkynylchlorobromo- and alkynyldibromomethanes, their multiplicity and philicity

  摘要：

  The action of t-BuOK on alkynyldihalomethanes RC=CCHBrX (I, R = Me, t-Bu, Ph; X = Br, Cl) in pentane at -20 to 0-degrees-C generates the corresponding alkynylhalocarbenes RC=CCX (II; X = Br, Cl) which in the presence of olefins give alkynylhalocyclopropanes (V) in 26-70% yield. It has been shown for the example of the reaction of (methylethynyl-) and (tert-butylethynyl)bromocarbenes with cis-butene-2 that the cycloaddition is fully stereospecific. The selectivity index for (methylethynyl)bromocarbene was experimentally determined as 0.48 which is evident for electrophilic character in this carbene.

  DOI：

  10.1007/bf00961044
• 作为产物：
  描述：

  4,4-dimethylpent-2-yn-1-ol 在 吡啶 、 chromium(VI) oxide 、 盐酸 、 溴 、 三氯化磷 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 1-bromo-1-chloro-4,4-dimethylpentyne-2
  参考文献：
  名称：

  Alkynylhalocarbenes 1. Generation of alkynylchloro- and alkynylbromocarbenes from alkynylchlorobromo- and alkynyldibromomethanes, their multiplicity and philicity

  摘要：

  The action of t-BuOK on alkynyldihalomethanes RC=CCHBrX (I, R = Me, t-Bu, Ph; X = Br, Cl) in pentane at -20 to 0-degrees-C generates the corresponding alkynylhalocarbenes RC=CCX (II; X = Br, Cl) which in the presence of olefins give alkynylhalocyclopropanes (V) in 26-70% yield. It has been shown for the example of the reaction of (methylethynyl-) and (tert-butylethynyl)bromocarbenes with cis-butene-2 that the cycloaddition is fully stereospecific. The selectivity index for (methylethynyl)bromocarbene was experimentally determined as 0.48 which is evident for electrophilic character in this carbene.

  DOI：

  10.1007/bf00961044

文献信息

• Shavrin, Konstantin N.; Krylova, Irina V.; Shvedova, Inna B., Journal of the Chemical Society. Perkin transactions II, 1991, # 12, p. 1875 - 1882
  作者：Shavrin, Konstantin N.、Krylova, Irina V.、Shvedova, Inna B.、Okonnishnikova, Galina P.、Dolgy, Igor E.、Nefedov, Oleg M.

  DOI：——

  日期：——
• Alkynylhalocarbenes 1. Generation of alkynylchloro- and alkynylbromocarbenes from alkynylchlorobromo- and alkynyldibromomethanes, their multiplicity and philicity
  作者：K. N. Shavrin、I. B. Shvedova、O. M. Nefedov

  DOI：10.1007/bf00961044

  日期：1991.11

  The action of t-BuOK on alkynyldihalomethanes RC=CCHBrX (I, R = Me, t-Bu, Ph; X = Br, Cl) in pentane at -20 to 0-degrees-C generates the corresponding alkynylhalocarbenes RC=CCX (II; X = Br, Cl) which in the presence of olefins give alkynylhalocyclopropanes (V) in 26-70% yield. It has been shown for the example of the reaction of (methylethynyl-) and (tert-butylethynyl)bromocarbenes with cis-butene-2 that the cycloaddition is fully stereospecific. The selectivity index for (methylethynyl)bromocarbene was experimentally determined as 0.48 which is evident for electrophilic character in this carbene.