(1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl chloride | 206190-78-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl chloride
• 英文别名: (1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl chloride
• CAS: 206190-78-5
• 化学式: C₁₁H₁₆ClNO₃S
• 分子量: 277.772
• InChiKey: KYBKCGAXCQRPHL-SOCHQFKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl chloride 在 sodium azide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 32.0h， 生成 (1R,5S)-4-[(1-methyl-7-azabicyclo[4.1.0]hept-7-yl)carbonyl]-10,10-dimethyl-3-thia-4-azatricyclo[5.2.1.0^1,5]decane-3,3-dioxide
  参考文献：
  名称：

  新型光学活性氨基甲酰基叠氮化物的合成及其作为胺化剂的用途

  摘要：

  描述了衍生自Oppolzer's sultam的手性氨基甲酰基叠氮化物的合成。还报道了在存在简单的烯烃以及被掩盖的酮的情况下的热和光化学行为。已经观察到非对映选择性胺化反应产生不同的产物。

  DOI：

  10.1016/s0040-4020(01)00383-0
• 作为产物：
  描述：

  (2R)-bornane-10,2-sultam 、 氯甲酸三氯甲酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 生成 (1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3lambda6-thia-4-azatricyclo[5.2.1.01,5]decane-4-carbonyl chloride
  参考文献：
  名称：

  Radical Reaction Initiated and Stereocontrolled by Zinc Chloride

  摘要：

  The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5a) was accelerated at -50 degrees C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78 degrees C in the presence of ZnCl2 . OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2 . OEt2, the reaction afforded methyl (2R)-2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3- carbamoyl)amino]4-pentenoate {6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2 . OEt2 works as a radical initiator as well as chelating agent.

  DOI：

  10.3987/com-97-s(n)71

文献信息

• New acylnitroso compounds for the asymmetric oxyamination of dienes
  作者：V. Gouverneur、S.J. McCarthy、C. Mineur、D. Belotti、G. Dive、L. Ghosez

  DOI：10.1016/s0040-4020(98)00504-3

  日期：1998.8

  A series of new enantiomerically pure acylnitroso compounds have been prepared and tested as dienophiles for the asymmetric oxyamination of dienes. Very high selectivities were obtained with acylnitroso compounds derived from diphenylmethoxymethyl pyrrolidine 2c, the C-2-symmetric pyrrolidines 2d-e and camphorsultam 2f. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Asymmetric synthesis of Boc-β2-homophenylglycine
  作者：Rachel Ponsinet、Gérard Chassaing、Solange Lavielle

  DOI：10.1016/s0957-4166(98)00036-6

  日期：1998.3

  Enantiomerically pure Boc-beta(2)-homophenylglycine has been prepared in five steps starting from Oppolzer's sultam. The key step of this route is the acylation of metalated phenylacetonitrile with sultam carbonyl chloride. Subsequent reactions (reduction, N-Boc protection, oxidation of the Boc-amino alcohol) led to Boc-(S)-beta(2)-HPhg starting from (+)-sultam. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis of a new optically active carbamoyl azide and its use as an aminating agent
  作者：Giuseppe Del Signore、Stefania Fioravanti、Lucio Pellacani、Paolo A Tardella

  DOI：10.1016/s0040-4020(01)00383-0

  日期：2001.5

  The synthesis of a chiral carbamoyl azide derived from Oppolzer's sultam is described. The thermal and photochemical behaviour in the presence of simple alkenes as well as of masked ketones is also reported. Diastereoselective amination reactions have been observed giving different products.

  描述了衍生自Oppolzer's sultam的手性氨基甲酰基叠氮化物的合成。还报道了在存在简单的烯烃以及被掩盖的酮的情况下的热和光化学行为。已经观察到非对映选择性胺化反应产生不同的产物。
• Radical Reaction Initiated and Stereocontrolled by Zinc Chloride
  作者：Yoshinori Yamamoto、Setsuko Onuki、Masatoshi Yumoto、Naoki Asao

  DOI：10.3987/com-97-s(n)71

  日期：——

  The reaction of allyltributyltin with methyl 2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3-carbamoyl)amino]-2-bromoacetate (5a) was accelerated at -50 degrees C in the presence of AIBN and stopped in the presence of galvinoxyl, indicating that the reaction proceeds through a radical mechanism. The reaction was accelerated dramatically at -78 degrees C in the presence of ZnCl2 . OEt2, and the ZnCl2-mediated reaction was stopped in the presence of galvinoxyl. In the presence of 2 equiv ZnCl2 . OEt2, the reaction afforded methyl (2R)-2-[N-((4S)-4-(1-methylethyl)-2-oxazolidinone-3- carbamoyl)amino]4-pentenoate 6a(R)} with high diastereoselectivity (93:7). Taken together, ZnCl2 . OEt2 works as a radical initiator as well as chelating agent.