(+)-10-<(Dibenzylamino)sulfonyl>bornan-6-one | 156730-39-1

• 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: (+)-10-<(Dibenzylamino)sulfonyl>bornan-6-one
• 英文别名: N,N-dibenzyl-1-((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonamide；N,N-dibenzyl-1-[(1S,4R)-7,7-dimethyl-2-oxo-1-bicyclo[2.2.1]heptanyl]methanesulfonamide
• CAS: 156730-39-1
• 化学式: C₂₄H₂₉NO₃S
• 分子量: 411.565
• InChiKey: MFTAVTKWZBBTJM-ZJSXRUAMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  62.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (+)-10-<(Dibenzylamino)sulfonyl>bornan-6-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 以92%的产率得到(+)-10-<(Dibenzylamino)sulfonyl>bornan-6-ol
  参考文献：
  名称：

  Studies on s-Cis/s-Trans Preference of Acyclic .alpha.,.beta.-Unsaturated Esters. Reactions, Supersonic Jet Spectroscopy, NOEs, and X-ray Analysis

  摘要：

  The s-cis/s-trans preference of acyclic alpha,beta-unsaturated esters has been studied by their reactions to elucidate the preference in the transition state and by supersonic jet spectroscopy, NOE experiments, and X-ray analysis to clarify the preference in the ground state. It has been widely accepted that enoate-Lewis acid complexes prefer the s-trans conformation not only in the ground state but also in the transition state of the reactions involving those complexes. The conjugate addition of metal amides to uncomplexed enoates proceeds predominantly through the s-cis conformation, and most organocopper conjugate additions in the absence of Lewis acids or related metal salts take place preferentially in the s-cis conformation. It is clarified that the relative population of the s-cis and s-trans conformer of uncomplexed methyl cinnamate is nearly 1:1 in a supersonic free jet and in solution at room temperature. X-ray analyses of 23 and 24 indicate the s-cis conformation, suggesting that most enoates adopt the s-cis form in the solid state except for 16-18.

  DOI：

  10.1021/jo00094a013
• 作为产物：
  描述：

  右旋樟脑-10-磺酰氯 、 二苄胺 在 异喹啉 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以78%的产率得到(+)-10-<(Dibenzylamino)sulfonyl>bornan-6-one
  参考文献：
  名称：

  Studies on s-Cis/s-Trans Preference of Acyclic .alpha.,.beta.-Unsaturated Esters. Reactions, Supersonic Jet Spectroscopy, NOEs, and X-ray Analysis

  摘要：

  The s-cis/s-trans preference of acyclic alpha,beta-unsaturated esters has been studied by their reactions to elucidate the preference in the transition state and by supersonic jet spectroscopy, NOE experiments, and X-ray analysis to clarify the preference in the ground state. It has been widely accepted that enoate-Lewis acid complexes prefer the s-trans conformation not only in the ground state but also in the transition state of the reactions involving those complexes. The conjugate addition of metal amides to uncomplexed enoates proceeds predominantly through the s-cis conformation, and most organocopper conjugate additions in the absence of Lewis acids or related metal salts take place preferentially in the s-cis conformation. It is clarified that the relative population of the s-cis and s-trans conformer of uncomplexed methyl cinnamate is nearly 1:1 in a supersonic free jet and in solution at room temperature. X-ray analyses of 23 and 24 indicate the s-cis conformation, suggesting that most enoates adopt the s-cis form in the solid state except for 16-18.

  DOI：

  10.1021/jo00094a013

文献信息

• A Broad‐Spectrum Catalytic Amidation of Sulfonyl Fluorides and Fluorosulfates**
  作者：Mingjie Wei、Dacheng Liang、Xiaohui Cao、Wenjun Luo、Guojian Ma、Zeyuan Liu、Le Li

  DOI：10.1002/anie.202013976

  日期：2021.3.22

  A broad‐spectrum, catalytic method has been developed for the synthesis of sulfonamides and sulfamates. With the activation by the combination of a catalytic amount of 1‐hydroxybenzotriazole (HOBt) and silicon additives, amidations of sulfonyl fluorides and fluorosulfates proceeded smoothly and excellent yields were generally obtained (87–99 %). Noticeably, this protocol is particularly efficient for

  已经开发了一种广谱催化方法，用于合成磺酰胺和氨基磺酸盐。通过催化量的1-羟基苯并三唑（HOBt）和硅添加剂的结合活化，磺酰氟和氟代硫酸盐的酰胺化反应顺利进行，通常获得优异的收率（87–99％）。值得注意的是，该协议对于空间受阻的底物特别有效。催化剂的负载量通常很低，而金刚烷衍生物的十克级合成仅需要0.02 mol％的催化剂。此外，通过关键中间体磺酰氟13合成市售药物Fedratinib，已证明了该方法在药物化学中的潜力。。由于大量的胺是可商购的，因此该途径提供了进入Fedratinib类似物进行生物学筛选的简便途径。
• Shida Naomi, Kabuto Chizuko, Niwa Taeko, Ebata Takayuki, Yamamoto Yoshino+, J. Org. Chem, 59 (1994) N 15, S 4068- 4075
  作者：Shida Naomi, Kabuto Chizuko, Niwa Taeko, Ebata Takayuki, Yamamoto Yoshino+

  DOI：——

  日期：——
• Studies on s-Cis/s-Trans Preference of Acyclic .alpha.,.beta.-Unsaturated Esters. Reactions, Supersonic Jet Spectroscopy, NOEs, and X-ray Analysis
  作者：Naomi Shida、Chizuko Kabuto、Taeko Niwa、Takayuki Ebata、Yoshinori Yamamoto

  DOI：10.1021/jo00094a013

  日期：1994.7

  The s-cis/s-trans preference of acyclic alpha,beta-unsaturated esters has been studied by their reactions to elucidate the preference in the transition state and by supersonic jet spectroscopy, NOE experiments, and X-ray analysis to clarify the preference in the ground state. It has been widely accepted that enoate-Lewis acid complexes prefer the s-trans conformation not only in the ground state but also in the transition state of the reactions involving those complexes. The conjugate addition of metal amides to uncomplexed enoates proceeds predominantly through the s-cis conformation, and most organocopper conjugate additions in the absence of Lewis acids or related metal salts take place preferentially in the s-cis conformation. It is clarified that the relative population of the s-cis and s-trans conformer of uncomplexed methyl cinnamate is nearly 1:1 in a supersonic free jet and in solution at room temperature. X-ray analyses of 23 and 24 indicate the s-cis conformation, suggesting that most enoates adopt the s-cis form in the solid state except for 16-18.