1,1,2-tribromo-2-butylcyclopropane | 157978-75-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: 1,1,2-tribromo-2-butylcyclopropane
• 英文别名: 1,1,2-tribromo-2-n-butylcyclopropane
• CAS: 157978-75-1
• 化学式: C₇H₁₁Br₃
• 分子量: 334.876
• InChiKey: UZMOVVZYOFIQFC-UHFFFAOYSA-N

物化性质

• 沸点：
  245.8±30.0 °C(Predicted)
• 密度：
  2.044±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1,1,2-tribromo-2-butylcyclopropane 在 六甲基磷酰三胺 、 正丁基锂 作用下， 以 水 、 丙酮 为溶剂， 生成 10-(2-Butyl-cycloprop-1-enyl)-decanenitrile
  参考文献：
  名称：

  Structure−Activity Relationships of Cyclopropene Compounds, Inhibitors of Pheromone Biosynthesis in Bombyx mori

  摘要：

  According to the synthetic route for 11,12-methylenehexadec-11-enoic acid [10-(2-butyl-1-cyclopropenyl)decanoic acid] and the amide, their related cyclopropene compounds, which possessed a propene ring at the 7,8-, 9,10-, or 13,14-position in a C-16 chain and the 11,12-position in a C-14 or C-18 chain, were synthesized via the corresponding 1-alkyl-1,2,2-tribromocyclopropane. Their activities as biosynthetic inhibitors of bombykol [(10E,12Z)-10,12-hexadecadien-1-ol; sex pheromone of the silkworm moth Bombyx mori L.] were measured with virgin female silkworm moths in vivo. The 7,8-methylene compounds were inactive even at the dose of 10 mu g/gland, but other compounds at 1 mu g/gland inhibited the conversion of [16,16, 16-H-2(3)]hexadecanoic acid to bombykol to some extent. Each amide showed stronger inhibitory activity than the corresponding acid, and the 11,12-methylene amide with a C-16 chain was the strongest (I-50 = 0.016 mu g/gland) among the tested compounds. Furthermore, experiments comparing the incorporation of [1-C-14]hexadecanoic acid into bombykol and another alcohol component in the pheromone gland, (Z)-11-hexadecen-1-ol, suggested that the all-desaturation was blocked by 9,10- and 11,12-methylene compounds and the subsequent Delta 10,- 12-desaturation by 11,12- and 13,14-methylene compounds.

  DOI：

  10.1021/jf950757n
• 作为产物：
  描述：

  1-己炔 在 sodium hydroxide 、 四乙基溴化铵 、 氢溴酸 、 十六烷基三甲基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1,1,2-tribromo-2-butylcyclopropane
  参考文献：
  名称：

  基于结构的对昆虫行为的干扰-含Z烯烃的信息素的环丙烯类似物

  摘要：

  合成了三种昆虫的信息素的类似物（家蝇，小菜蛾和小菜蛾），其中Z-烯烃已被1,2-二取代的环丙烯代替。这些类似物会干扰每个物种的正常交配行为。

  DOI：

  10.1016/0040-4020(96)00730-2

文献信息

• Cyclopropenylcarbinol Derivatives as New Versatile Intermediates in Organic Synthesis: Application to the Formation of Enantiomerically Pure Alkylidenecyclopropane Derivatives
  作者：Samah Simaan、Ahmad Masarwa、Elinor Zohar、Amnon Stanger、Philippe Bertus、Ilan Marek

  DOI：10.1002/chem.200901074

  日期：2009.8.24

  The copper‐catalyzed carbomagnesiation (or hydrometalation) reaction of chiral cyclopropenylcarbinol derivatives, obtained by means of a kinetic resolution of secondary allylic alcohols, leads to an easy and straightforward preparation of enantiomerically pure alkylidenecyclopropane derivatives. The reaction mechanism is composed of a syn‐carbometalation followed by a syn‐elimination reaction. To gain

  通过仲烯丙醇的动力学拆分获得的手性环丙烯基甲醇衍生物的铜催化碳镁化（或加氢金属化）反应可以简单直接地制备对映体纯的亚烷基环丙烷衍生物。反应机理是顺式碳金属化，然后是顺式-消除反应。为了进一步了解碳金属化的反应机理，还实现了环丙基甲醇的非对映选择性形成，并且发现它对用于加成反应的有机金属物质的性质非常敏感。环丙醇也可以通过环丙烯基甲醇衍生物的非对映选择性还原来制备。最后，在温和条件下，将富含对映异构体的环丙烯基甲醇官能化为相应的乙酸酯或亚膦酸酯衍生物会导致各种对映异构体纯杂取代的亚烷基环丙烷。
• Structure based interference with insect behaviour - cyclopropene analogues of pheromones containing Z-alkenes
  作者：Juma'a R. Al Dulayymi、Mark S. Baird、Michael J. Simpson、Susan Nyman、Gordon R. Port

  DOI：10.1016/0040-4020(96)00730-2

  日期：1996.9

  Analogues of the pheromones of three insect species (Musca domestica L., Plutella xylostella L. and Ephestia elutella Hbn.) in which a Z-alkene has been replaced by a 1,2-disubstituted cyclopropene have been synthesised. The analogues interfere with normal mating behaviour for each species.

  合成了三种昆虫的信息素的类似物（家蝇，小菜蛾和小菜蛾），其中Z-烯烃已被1,2-二取代的环丙烯代替。这些类似物会干扰每个物种的正常交配行为。
• Cyclopropenyllithiums as a new source of 1,1-bismetalated cyclopropyl derivatives
  作者：Anat Levin、Ilan Marek

  DOI：10.1039/b807635a

  日期：——

  The allylmetalation of functionalised cyclopropenyllithium derivatives leads to the unique formation of 1,1-bismetalated cyclopropyl species that react selectively with different electrophiles.

  功能化环丙烯锂衍生物的烯丙基金属化反应导致独特的1,1-双金属化环丙基物种的形成，这些物种能与不同的电亲体选择性反应。
• Stereocontrolled approaches to 2-(2-aminoalkyl)-1-hydroxycyclopropanes
  作者：Mark S Baird、Florian A.M Huber、William Clegg

  DOI：10.1016/s0040-4020(01)00996-6

  日期：2001.12

  (1S,2S)-2[(S)-Amino(4-methoxyphenyl)methyl]cyclopropan-1-of together with a range of racemic 2-(2-aminoalkyl)-1-hydroxy-cyclopropanes were prepared by a stepwise procedure involving a 1,3-dipolar cycloaddition of a nitrile oxide to a cyclopropene followed by reduction of the derived bicycle. (C) 2001 Elsevier Science Ltd. All rights reserved.

  (1S,2S)-2[(S)-氨基(4-甲氧基苯基)甲基]环丙烷-1-酮，以及一系列2-(2-氨基烷基)-1-羟基环丙烷的外消旋体，通过分步工艺制得，该工艺涉及硝基氧化物与环丙烯的1,3-偶极环加成反应，随后对产生的双环化合物进行还原。 (C) 2001 Elsevier Science Ltd. 保留所有权利。
• Pyridazines by addition of diazoalkanes to 1-bromo- and 1,2-dibromocyclopropenes
  作者：Ahmad R. Al Dulayymi、Mark S. Baird

  DOI：10.1016/s0040-4020(98)00781-9

  日期：1998.10

  Reaction of a range of 1-bromocyclopropenes with diazo-compounds leads to pyrazoles which ring-open to pyridazines in reasonable yield.

  一系列的1-溴环丙烯与重氮化合物的反应生成吡唑，其以合理的收率对哒嗪开环。