1,1-二溴-2-丁基环丙烷 | 5398-70-9

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 中文名称: 1,1-二溴-2-丁基环丙烷
• 英文名称: 1,1-dibromo-2-butylcyclopropane
• 英文别名: 1,1-dibromo-2-butyl-cyclopropane；1,1-Dibrom-2-butyl-cyclopropan
• CAS: 5398-70-9
• 化学式: C₇H₁₂Br₂
• 分子量: 255.98
• InChiKey: MNKZKQIKLRLXOW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  9
• 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：

  1,1-二溴-2-丁基环丙烷 在 chromium(VI) oxide 、 溶剂黄146 作用下， 反应 72.0h， 以36%的产率得到2,2-二溴环丙烷-1-羧酸
  参考文献：
  名称：

  Unusual selectivity in the oxidative functionalization of gem-dibromocyclopropanes

  摘要：

  Oxidation of gem-dibromocyclopropanes with chromium trioxide in acetic acid or a number of other reagents is generally slower than that of the corresponding cyclopropane; in a number of cases moderate yields of products are obtained but these show unexpected oxidation patterns. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2004.02.024
• 作为产物：
  描述：

  1-庚烯 在 sodium hydroxide 、 三溴甲烷 作用下， 以 二氯甲烷 为溶剂， 生成 1,1-二溴-2-丁基环丙烷
  参考文献：
  名称：

  Preparation of allyl alcohols from monohalo- and gem-dihalobutylcyclopropanes in the presence of copper and its salt

  摘要：

  The reaction of gem-dibromo- or gem-dichlorobutylcyclopropanes with an equimolar amount of CuSO4 . 5H2O in a mixture of DMSO and water is accompanied by scission of the three-membered ring and formation of the corresponding 2-bromo- or 2-chloroallyl alcohols. The corresponding allyl alcohols were prepared analogously from monobromo- or monochlorocyclopropanes.

  DOI：

  10.1007/bf00961036

文献信息

• Electrochemical oxidation of alkyl-substituted allenes in methanol
  作者：James Y. Becker、Baruch Zinger

  DOI：10.1016/0040-4020(82)80146-4

  日期：1982.1

  di- and tri-alkyl-substituted allenes were potentiostatically oxidized in methanol at graphite and Pt anodes. At the former electrode, α-methoxylated ketones (due to 4F/mole electricity consumption) and esters (6F/mole) were the major products. At a Pt anode, intermediate products such as vinyl-ether derivatives (2F/mole) were characterised too. Unlike the anodic oxidation of alkenes and alkynes previously

  在甲醇和石墨阳极上，单，二和三烷基取代的烯基在甲醇中被恒电位氧化。在前一个电极上，主要产品是α-甲氧基化的酮（由于消耗4F /摩尔）和酯（6F /摩尔）。在铂阳极上，也表征了中间产物，如乙烯基醚衍生物（2F /摩尔）。与先前文献中所记载的烯烃和炔烃的阳极氧化不同，二聚化不是艾伦烯氧化的典型过程，因为已观察到所有产物均仅观察到单一的二聚体。讨论了大多数产品形成的机理。
• New synthesis of β-lactams
  作者：M. Mori、K. Chiba、M. Okita、I. Kayo、Y. Ban

  DOI：10.1016/s0040-4020(01)96429-4

  日期：1985.1

  α-Methylene-β-lactams 3 were synthesized from the various 2-bromoallylamine derivatives 2 using a catalytic amount of Pd(OAc)2 or PD(acac)2 and PPh3, under 1–4 atom pressure of CO in good yields. Similarly, α-alkylidene-β-lactams 20 were synthesized from 3-alkyl-2-bromoallylamines 19, which were easily prepared from the olefins 14, in the same manner.

  在1-4个CO原子压力下，使用催化量的Pd（OAc）2或PD（acac）2和PPh 3由各种2-溴烯丙胺衍生物2合成α-亚甲基-β-内酰胺3。类似地，由3-烷基-2-溴烯丙基胺19合成α-亚烷基-β-内酰胺20，所述3-烷基-2-溴烯丙基胺以相同的方式容易地由烯烃14制备。
• Reaction behavior of cyclopropylmethyl cations derived 1-phenylselenocyclopropylmethanols with acids
  作者：Mitsunori Honda、Toshiaki Nishizawa、Yuko Nishii、Shuhei Fujinami、Masahito Segi

  DOI：10.1016/j.tet.2009.08.082

  日期：2009.11

  ropylmethyl cations are generated by the reaction of the corresponding cyclopropylmethanols 1 with TsOH. The reaction in methanol proceeds to afford the homoallylic ethers 2, ring-enlargement products 3, 4, and ring opening products 5 depending upon the kind of substituent on the cyclopropane ring or the α-carbon. On the other hand, in the case of the absence of methanol as nucleophile, 4H-selenochromene

  通过相应的环丙基甲醇1与TsOH的反应生成1-苯基硒代环丙基甲基阳离子。在甲醇中进行反应，得到高烯丙基醚2，环增大产品3，4，和开环产品5取决于环丙烷环或α碳原子上取代基的种类。另一方面，在不存在甲醇作为亲核试剂的情况下，仅获得4 H-硒代色烯衍生物7。所得苯硒基均烯丙基化合物2中苯硒基的氧化消除 提供官能化的丙二烯衍生物和炔烃衍生物。
• Optimized synthesis of 2-substituted 1-halocyclopropane-1-carboxylic acids
  作者：A. A. Zagidullin、A. V. Zorin、V. V. Zorin

  DOI：10.1134/s1070363216100108

  日期：2016.10

  gem-dibromocyclopropanes with n-butyllithium in THF under argon at–78°С followed by purging the reaction mixture with dry CO2 was used to synthesize cis- and/or trans-1-halocyclopropane-1-carboxylic acids in 30–56% yields. The yields of the target products could be increased to 76–83% by the addition of an equimolar amount of LiCl to the reaction mixture. The highest salt effect was obtained with lithium

  在氩气下于–78°C下，使宝石-二氯和宝石-二溴环丙烷与正丁基锂在THF中反应，然后用干燥的CO 2吹扫反应混合物，以合成顺式和/或反式-1-卤代环丙烷-1 -羧酸的收率为30–56％。通过向反应混合物中添加等摩尔量的LiCl，可以将目标产物的收率提高到76-83％。用原位生成的氯化锂可获得最高的盐效应（88–96％）。
• The Nickel and Palladium Catalysed Stereoselective Cross Coupling of Cyclopropyl Nucleophiles with Aryl Halides
  作者：R.-J. de Lang、L. Brandsma

  DOI：10.1080/00397919808005715

  日期：1998.1

  Abstract The reaction of 2-phenylcyclopropylzinc chloride with some substituted (het)aryl halides gave the corresponding coupling products with good yields and stereoselectivities under the influence of a catalytic amount of Pd(PPh3)4. Other Ni-and Pd-catalysts were less efficient. Alkyl-substituted cyclopropyl nucleophiles gave lower yields.

  摘要 在催化量的Pd(PPh3)4 作用下，2-苯基环丙基氯化锌与一些取代的(杂)芳基卤化物反应得到相应的偶联产物，具有良好的产率和立体选择性。其他 Ni 和 Pd 催化剂效率较低。烷基取代的环丙基亲核试剂的产率较低。