1-chloro-1-(1-adamantylethinyl)-2,2-dimethylcyclopropane | 139185-62-9

• 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-chloro-1-(1-adamantylethinyl)-2,2-dimethylcyclopropane
• 英文别名: 1-[2-(1-Chloro-2,2-dimethylcyclopropyl)ethynyl]adamantane
• CAS: 139185-62-9
• 化学式: C₁₇H₂₃Cl
• 分子量: 262.823
• InChiKey: QVLKJFIEHUWZIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.88
• 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：

  1-chloro-1-(1-adamantylethinyl)-2,2-dimethylcyclopropane 在 lithium diethylamide 作用下， 以 四氢呋喃 为溶剂， 生成 4-(3-adamantyl-ethynyl-2,2-dimethylcyclopropyl)morpholine
  参考文献：
  名称：

  1-(Alk-1-ynyl)cyclopropenes: synthesis by interaction of 1-(alk-1-ynyl)-1-halocyclopropanes with lithium N,N-dialkylamides and subsequent additions of the latter

  摘要：

  A new synthetic approach to 1-(alk-1-ynyl)cyclopropenes 2 by the reaction of 1-(alk-1-ynyl)-1-chlorocyclopropanes 1 with lithium N,N-dialkylamides has been developed. Alkynylcyclopropenes 2, obtained by this method in situ or isolated in individual state can add dialkylamide anions across the double bond of the cyclopropene fragment to give hitherto unknown alkynyl(dialkylamino)cyclopropanes 3, 4.

  DOI：

  10.1070/mc2006v016n02abeh002267
• 作为产物：
  描述：

  3-(1-Adamantyl)prop-2-ynal 在 吡啶 、 氢氧化钾 、 五氯化磷 、 苄基三乙基氯化铵 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 3.33h， 生成 1-chloro-1-(1-adamantylethinyl)-2,2-dimethylcyclopropane
  参考文献：
  名称：

  Alkynylhalocarbenes. 2. Generation of (alkyn-1-yl)-chlorocarbenes by basic solvolysis of 1,1-dichloro-2-alkynes and their reaction with olefins: Synthesis of 1-chloro-1-alkynylcyclopropanes

  摘要：

  1,1-Dichloro-2-alkynes R1C=CCHCl2 (4a-g; R1 = Me, n-Pr, c-Pr, t-Bu, Ad, Nor, Ph) were synthesized with yield of 50-75% by chlorination with PCl5 of formylacetylenes (3a-g), prepared by oxidation of propargyl alcohols (1a-d) with CrO3.Py.HCl complex or acidolysis of propargyl acetals (2a-c) in the presence of catalytic quantities of pyridine; the corresponding alkynylchlorocarbenes, R1C=CCCl (5a-g) were generated from them with powdered KOH in a two-phase system or t-BuOK. The latter were trapped by olefins with formation of 1-chloro-1-alkynylcyclopropanes (6a-t) with yields of up to 90%.

  DOI：

  10.1007/bf00864534

文献信息

• Synthesis of 1-alkynyl-2-dialkylaminocyclopropanes and 1-alkynyl-2-diazolylcyclopropanes by reactions of 1-alkynyl-1-chlorocyclopropanes with amines and their lithium derivatives
  作者：K. N. Shavrin、V. D. Gvozdev、O. M. Nefedov

  DOI：10.1007/s11172-010-0092-5

  日期：2010.2

  Reactions of 1-alkynyl-1-chlorocyclopropanes with lithium dialkylamides gave previously unknown 1-alkynyl-2-dialkylaminocyclopropanes. 1-(Alk-1-ynyl)-2-diazolylcyclopropanes were obtained by reactions of 1-alkynyl-1-chlorocyclopropanes with diazoles in the presence of KOH in DMSO at 100 °C. These reactions passed through the formation of conjugated alky-nylcyclopropenes and reversible addition of amide

  1-炔基-1-氯环丙烷与二烷基酰胺锂的反应得到了以前未知的1-炔基-2-二烷基氨基环丙烷。1-(Alk-1-ynyl)-2-二唑基环丙烷是通过 1-炔基-1-氯环丙烷与二唑在 KOH 存在下在 DMSO 中于 100 °C 反应获得的。这些反应通过共轭烷基-烷基环丙烯的形成和酰胺阴离子的可逆加成进行。这些转化的区域选择性和立体选择性取决于起始氯环丙烷和胺中的取代基。
• 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：——
• Unusual reactions of 1-(alk-1-ynyl)-1-chlorocyclopropanes with lithium monoalkylamides
  作者：Konstantin N. Shavrin、Valentin D. Gvozdev、Serafim V. Yurov、Oleg M. Nefedov

  DOI：10.1016/j.mencom.2008.01.007

  日期：2008.1

  Depending on the substituent at the triple bond, the reaction of 1-(alk-1-ynyl)-1-chlorocyclopropanes 1 with lithium monoalkylamides in THF gives hitherto unknown conjugated iminocyclopropenes 2 or 4-substituted 1,1-dimethylbuta-1,2-dienes 3 in up to 60% yields.