2,2-二溴环丙烷-1-羧酸 | 5365-17-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: 2,2-二溴环丙烷-1-羧酸
• 英文名称: 2,2-dibromocyclopropanecarboxylic acid
• 英文别名: 2,2-dibromocyclopropane-1-carboxylic acid
• CAS: 5365-17-3
• 化学式: C₄H₄Br₂O₂
• 分子量: 243.883
• InChiKey: ZZQWHIVRLNQEDZ-UHFFFAOYSA-N

物化性质

• 熔点：
  94-95 °C(Solv: hexane (110-54-3))
• 沸点：
  302.7±42.0 °C(Predicted)
• 密度：
  2.632±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,2-二溴环丙烷-1-羧酸 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到2,2-dibromocyclopropane-1-methanol
  参考文献：
  名称：

  Sydnes, Leiv K.; Pereira, Paula F. F.; Sandberg, Marcel, Journal of Chemical Research, Miniprint, 2001, # 4, p. 464 - 474

  摘要：

  DOI：
• 作为产物：
  描述：

  2,2-dibromocyclopropane-1-methanol 在 potassium permanganate 、 四丁基溴化铵 作用下， 以 水 、 苯 为溶剂， 反应 16.0h， 以91%的产率得到2,2-二溴环丙烷-1-羧酸
  参考文献：
  名称：

  摘要：

  Cyclopent-2-en-1-one is a versatile electrophilic cyclopentadiene equivalent in reactions with 1-bromo-1-lithiocyclopropanes. The synthetic sequence (outlined in Scheme 1) has been applied to the synthesis of functionalized 7-X-7,8-dihydrocalicenes 13c (Scheme 3) and 13d (Scheme 4). 7-Bromo-7,8-dihydrocalicene (13d) is considered to be a promising precursor of the so far unknown parent calicene (2). A similar sequence has been realized for 7-(chloromethyl)-7,8-dihydrocalicene (21a, Scheme 5) which, under appropriate conditions, could give 7-methylcalicene (16).

  DOI：

  10.1002/(sici)1522-2675(20000315)83:3<571::aid-hlca571>3.0.co;2-m

文献信息

• 6-(Substituted-cycloalkylcarboxamide) penicillanic acids
  申请人：Bayer Aktiengesellschaft

  公开号：US03954730A1

  公开（公告）日：1976-05-04

  Penicillins of the formula ##SPC1## Or a pharmaceutically-acceptable, nontoxic salt thereof, Wherein R.sub.1 and R.sub.2 are the same or different and each is hydrogen, fluorine, chlorine or bromine; or when R.sub.2 is hydrogen, R.sub.1 can also be cyano, hydroxyl, azido, amino or nitro; or R.sub.1 and R.sub.2 are bonded to a ring carbon atom and constitute a single oxygen atom; R.sub.3 is hydrogen, methyl, chlorine, bromine, cyano, methoxy or carboxyl; and n is 2 to 7; Are useful for their antibacterial activity.

  盐酸盐或药用可接受的非毒性盐的公式为##SPC1##的青霉素，其中R.sub.1和R.sub.2相同或不同，每个都是氢、氟、氯或溴；或者当R.sub.2是氢时，R.sub.1也可以是氰基、羟基、叠氮基、氨基或硝基；或者R.sub.1和R.sub.2连接到一个环碳原子并构成一个单氧原子；R.sub.3是氢、甲基、氯、溴、氰基、甲氧基或羧基；n为2到7；它们因其抗菌活性而有用。
• Formal Nucleophilic Substitution of Bromocyclopropanes with Amides en route to Conformationally Constrained β-Amino Acid Derivatives
  作者：Anthony R. Prosser、Joseph E. Banning、Marina Rubina、Michael Rubin

  DOI：10.1021/ol101228k

  日期：2010.9.17

  A chemo- and diastereoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides with secondary amides is described. This method allows for convergent and highly selective synthesis of trans-β-aminocyclopropane carboxylic acid derivatives.

  描述了用仲酰胺对2-溴环丙基羧酰胺进行正式亲核取代的化学和非对映选择性方案。该方法允许反式-β-氨基环丙烷羧酸衍生物的收敛和高度选择性的合成。
• Thermodynamic Control of Diastereoselectivity in the Formal Nucleophilic Substitution of Bromocyclopropanes
  作者：Joseph E. Banning、Anthony R. Prosser、Michael Rubin

  DOI：10.1021/ol100187c

  日期：2010.4.2

  A new, general, and chemoselective protocol for the formal nucleophilic substitution of 2-bromocyclopropylcarboxamides Is described. A wide range of alcohols and phenols can be employed as pronucleophiles in this transformation, providing expeditious access to trans-cyclopropanol ethers. A new mode of the selectivity control through a thermodynamic equilibrium is realized, alternative to the previously described steric and directing modes.
• Pettersen, Anita; Jorgensen, Evy; Sydnes, Leiv K., Acta Chemica Scandinavica, 1990, vol. 44, # 6, p. 603 - 609
  作者：Pettersen, Anita、Jorgensen, Evy、Sydnes, Leiv K.

  DOI：——

  日期：——
• Alnasleh, Bassam K.; Sherrill, William M.; Rubina, Marina, Journal of the American Chemical Society, 2009, vol. 131, p. 6906 - 6907
  作者：Alnasleh, Bassam K.、Sherrill, William M.、Rubina, Marina、Banning, Joseph、Rubin, Michael

  DOI：——

  日期：——