1-bromo-2,2-dichloro-1-methylcyclopropane | 14477-99-7

• 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-2,2-dichloro-1-methylcyclopropane
• CAS: 14477-99-7
• 化学式: C₄H₅BrCl₂
• 分子量: 203.894
• InChiKey: APJOAXUYDQWJHE-UHFFFAOYSA-N

物化性质

• 沸点：
  45-46 °C(Press: 16 Torr)
• 密度：
  1.79±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  7
• 可旋转键数：
  0
• 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：

  乙醇 、 1-bromo-2,2-dichloro-1-methylcyclopropane 在 sodium 作用下， 以 四氢呋喃 为溶剂， 以72%的产率得到3,3-diethoxy-but-1-yne
  参考文献：
  名称：

  Regiospecific Ring Opening of Some Methyl- and Phenyl-Substituted 1,1,2-Trihalocyclopropanes to Acetylenic Acetals or Ketals by Variation of Reaction Conditions.

  摘要：

  Regiospecific ring opening of six title compounds has been achieved under various reaction conditions. With dry sodium ethoxide in dry THF as reagent acetylenic diethyl ketals are obtained in 66-81% isolated yield. With DBU in dry ethanol, the corresponding acetylenic diethyl acetals are formed and isolated in 50-67% yield. Finally, treatment of the substrates with 50% aqueous sodium hydroxide in the presence of 2-propanol, triethylbenzylammonium chloride and dichloromethane gave acetylenic diisopropyl acetals, in 82% yield at the best. By-product formation was negligible in most cases.

  DOI：

  10.3891/acta.chem.scand.52-1029
• 作为产物：
  描述：

  氯仿 、 2-溴丙烯 在 苄基三乙基氯化铵 sodium hydroxide 作用下， 以44%的产率得到1-bromo-2,2-dichloro-1-methylcyclopropane
  参考文献：
  名称：

  Pettersen, Anita; Jorgensen, Evy; Sydnes, Leiv K., Acta Chemica Scandinavica, 1990, vol. 44, # 6, p. 603 - 609

  摘要：

  DOI：

文献信息

• CYCLOPROPENES-GENERATING DEVICES TO CONTROL RIPENING PROCESSES OF AGRICULTURAL PRODUCTS
  申请人：YOO Sang-Ku

  公开号：US20120130104A1

  公开（公告）日：2012-05-24

  Provided is a device for generation of cyclopropene compounds which is capable of achieving direct in situ preparation and application of cyclopropene compounds inhibiting the action of ethylene which accelerates the ripening process of plants, the device comprising a first storage part for storing precursors of cyclopropene compounds (“cyclopropene precursors”), a second storage part for storing reaction reagents which convert cyclopropene precursors into cyclopropene derivatives via chemical reaction, and a spray part for spraying the cyclopropene derivatives produced by the chemical reaction between the cyclopropene precursors and the reaction reagents.

  提供的是一种用于生成环丙烯化合物的装置，能够实现环丙烯化合物的直接原位制备和应用，从而抑制乙烯的作用，乙烯会加速植物的成熟过程。该装置包括用于存储环丙烯化合物前体（“环丙烯前体”的第一存储部分，用于存储将环丙烯前体通过化学反应转化为环丙烯衍生物的反应试剂的第二存储部分，以及用于喷洒由环丙烯前体和反应试剂之间的化学反应产生的环丙烯衍生物的喷雾部分。
• Reactions of dichlorocarbene and tri-chloromethide with O-alkenyl esters and ethers, N-vinyl amides, and 1-haloalkenes
  作者：R.C. De Selms、T.-W. Lin

  DOI：10.1016/0040-4020(67)85101-9

  日期：1967.1

  mixtures due to apparent addition of trichloromethide and dichlorocarbene. In general, the yields of gem-dichlorocyclopropanes increased with increasing alkyl substituents on the alkene substrates. A trend toward increasing yield of gem-dichlorocyclopropanes was also noticed with the following substituents on the alkene substrates: OP(O) (OR)2 < Halogen ≅ OC(O)R < OR ≅ NRC(O)R′. Evidence is presented

  据报道，由三氯乙酸钠产生的二氯卡宾和/或三氯甲烷在回流的1,2-二甲氧基乙烷中与各种脂族O-炔烃酯和醚，N-乙烯基酰胺和1-卤代烯烃反应的范围和局限性。所有组均给出了宝石-二氯环丙烷，唯一的例外是O-乙烯基羧酸酯，其中仅出现了三氯甲基化物的加成产物或由于明显添加了三氯甲基化物和二氯卡宾而形成的混合物。通常，宝石-二氯环丙烷的产率随着烯烃底物上烷基取代基的增加而增加。还发现在烯烃底物上带有以下取代基的宝石-二氯环丙烷的收率有增加的趋势：OP（O）（OR）2 <卤素OC（O）R <或ORNRC（O）R'。提供的证据表明质子的来源与三氯甲基甲烷的添加同时发生。详细介绍了一些取代的宝石-二氯环丙烷与LAH的反应。
• Cyclopropenes-Generating Devices to Control Ripenning Processes of Agricultural Products
  申请人：Yoo Sang-Ku

  公开号：US20080286426A1

  公开（公告）日：2008-11-20

  Provided is a device for generation of cyclopropene compounds which is capable of achieving direct in situ preparation and application of cyclopropene compounds inhibiting the action of ethylene which accelerates the ripening process of plants, the device comprising a first storage part for storing precursors of cyclopropene compounds (“cyclopropene precursors”), a second storage part for storing reaction reagents which convert cyclopropene precursors into cyclopropene derivatives via chemical reaction, and a spray part for spraying the cyclopropene derivatives produced by the chemical reaction between the cyclopropene precursors and the reaction reagents.

  提供的是一种用于生成环丙烯化合物的装置，能够直接进行原位制备和应用环丙烯化合物，抑制乙烯的作用，从而加速植物的成熟过程。该装置包括第一存储部分，用于存储环丙烯化合物的前体（“环丙烯前体”）；第二存储部分，用于存储反应试剂，通过化学反应将环丙烯前体转化为环丙烯衍生物；以及喷雾部分，用于喷洒由环丙烯前体和反应试剂之间的化学反应产生的环丙烯衍生物。
• Formation of Acetylenic Acetals by Ring Opening of 1,1,2-Trihalocyclopropanes under Phase-Transfer Conditions.
  作者：Leiv K. Sydnes、Einar Bakstad、Morten Heide、Georg W. Jensen、Inge L. Møller、Ruby I. Nielsen、Carl Erik Olsen、Connie N. Rosendahl、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0446

  日期：——

  A number of substituted 1,1-dibromo- and 1,1-dichlorocyclopropanes with an additional chlorine or bromine atom attached to C-2 were synthesized in reasonable to good yields by dihalocarbene addition to the corresponding alkenes under phase-transfer conditions. When the trihalides were treated with 50% aqueous sodium hydroxide in the presence of ethanol, triethylbenzylammonium chloride and dichloromethane, most of the compounds underwent ring opening and afforded mixtures of acetylenic acetals, usually in good yields. The reaction most likely involves cyclopropene intermediates, which in some cases also rearrange to a minor extent to the corresponding vinylcarbenes and afford alpha,beta-unsaturated aldehydes.
• PETTERSEN, ANITA;JZHUSTORGENSEN, EVU;SUDNES, LEIV K., ACTA CHEM. SCAND. , 44,(1990) N, C. 603-609
  作者：PETTERSEN, ANITA、JZHUSTORGENSEN, EVU、SUDNES, LEIV K.

  DOI：——

  日期：——