anti-7-Brom-syn-7-norcaranyl-carbonsaeure | 38213-14-8

• 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
• 英文名称: anti-7-Brom-syn-7-norcaranyl-carbonsaeure
• CAS: 38213-14-8
• 化学式: C₈H₁₁BrO₂
• 分子量: 219.078
• InChiKey: SYFAQQMTYSCLJX-BDINMYNLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  anti-7-Brom-syn-7-norcaranyl-carbonsaeure 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以64%的产率得到methyl exo-7-bromobicyclo[4.1.0]heptane-7-carboxylate
  参考文献：
  名称：

  Highly Stereoselective Radical Carbonylations of gem-Dihalocyclopropane Derivatives with CO

  摘要：

  A couple of radical carbonylations of gem-dihalocyclopropanes 1 using CO and Bu3SnH (formylation) or Bu3Sn(CH2CHCH2) (allylacylation) successfully proceeded to give trans and cis adducts (2 and 3) with good to excellent stereoselectivity (trans/cis = > 99/1-75/25 or 17/83-1/99). The formylation of 2,3-cis-disubstituted 1,1-dihalocyclopropanes enhanced trans selectivity (trans/cis = > 99/1-95/5), whereas both 2,3-cis-disubstituted and 2-monosubstituted 1,1-dihalocyclopropanes underwent allylacylation with nearly complete trans selectivity (trans/cis = > 99/1). Inherently less reactive gem-dichloro- and bromochlorocyclopropanes than gem-dibromocyclopropanes served as favorable substrates.

  DOI：

  10.1021/ol062673d
• 作为产物：
  描述：

  7,7-dibromonorcarane 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.5h， 生成 anti-7-Brom-syn-7-norcaranyl-carbonsaeure
  参考文献：
  名称：

  Highly Stereoselective Radical Carbonylations of gem-Dihalocyclopropane Derivatives with CO

  摘要：

  A couple of radical carbonylations of gem-dihalocyclopropanes 1 using CO and Bu3SnH (formylation) or Bu3Sn(CH2CHCH2) (allylacylation) successfully proceeded to give trans and cis adducts (2 and 3) with good to excellent stereoselectivity (trans/cis = > 99/1-75/25 or 17/83-1/99). The formylation of 2,3-cis-disubstituted 1,1-dihalocyclopropanes enhanced trans selectivity (trans/cis = > 99/1-95/5), whereas both 2,3-cis-disubstituted and 2-monosubstituted 1,1-dihalocyclopropanes underwent allylacylation with nearly complete trans selectivity (trans/cis = > 99/1). Inherently less reactive gem-dichloro- and bromochlorocyclopropanes than gem-dibromocyclopropanes served as favorable substrates.

  DOI：

  10.1021/ol062673d

文献信息

• Stereospecific routes to the isomeric 7-bromo-7-lithionorcaranes
  作者：Dietmar Seyferth、Robert L. Lambert

  DOI：10.1016/s0022-328x(00)82047-1

  日期：1973.7

  anti-7-Bromo-syn-7-lithionorcarane can be prepared stereospecifically by the reaction of n-butyllithium with 7,7-dibromonorcarane in THF, provided that a slight excess of the dibromo compound is present and the temperature is allowed to rise briefly from −107° to about −93°. syn-7-Bromo-anti-7-lithionorcarane results when n-butyllithium is allowed to react with syn-7-bromo-anti-7-trimethyltinnorearane

  可以通过正丁基锂与7,7-二溴呋喃烷在THF中的反应来立体定向制备抗-7-溴-顺式-7-锂呋喃烷，条件是存在稍微过量的二溴化合物，并允许温度短暂升高从-107°到大约-93°。顺-7-溴反当正丁基锂使之与反应-7- lithionorcarane结果顺-7-溴-反-7- trimethyltinnorearane在THF中在低温下。报道了这些试剂与Me 3 SiCl，Me 3 SnCl，CO 2和C 2 Cl 6的立体定向反应。
• Halomethyl—metal compounds
  作者：Dietmar Seyferth、Robert L. Lambert、Michel Massol

  DOI：10.1016/s0022-328x(00)89503-0

  日期：1975.4

  A number of α-bromocyclopropyllithium reagents have been prepared at low temperature (−90° to −100°) in THF or THF/Et2O medium by reaction of n-butyllithium with the respective gem-dibromocyclopropane. Reactions of these new lithium reagents with concentrated HCl, trimethylchlorosilane, dimethyldichlorosilane, trimethyltin chloride, dimethyltin dichloride, dimethyldichlorogermane, trimethyllead bromide

  通过正丁基锂与相应的宝石-二溴环丙烷的反应，已在THF或THF / Et 2 O介质中于低温（-90°至-100°）下制备了多种α-溴环丙基锂试剂。描述了这些新的锂试剂与浓盐酸，三甲基氯硅烷，二甲基二氯硅烷，三甲基氯化锡，二甲基锡二氯化物，二甲基二氯锗烷，三甲基溴化铅，氯化汞和一些其他有机金属卤化物的反应。的一种新的异构化顺式-7-溴-反-7- lithionorcarane到反-7-溴-顺-7- lithionorcarane，通过稍微过量的7,7- dibromonorcarane的存在引起的，进行说明。