(2S,3S)-3-Hydroxy-3-phenylethynyl-2-(toluene-4-sulfonylamino)-decanoic acid ethyl ester

• 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: (2S,3S)-3-Hydroxy-3-phenylethynyl-2-(toluene-4-sulfonylamino)-decanoic acid ethyl ester
• 英文别名: ethyl (2S,3S)-3-hydroxy-2-[(4-methylphenyl)sulfonylamino]-3-(2-phenylethynyl)decanoate
• 化学式: C₂₇H₃₅NO₅S
• 分子量: 485.645
• InChiKey: BHMDPSUZVJKDGX-VPUSJEBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  34
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S)-3-Hydroxy-3-phenylethynyl-2-(toluene-4-sulfonylamino)-decanoic acid ethyl ester 在 碘 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 以71%的产率得到
  参考文献：
  名称：

  A general approach to polysubstituted pyrroles

  摘要：

  Exposure of a range of 3-hydroxy-2-sulfonylamino-4-alkynes to excess iodine delivers good yields of a series of iodopyrroles. Unexpectedly, the hydroxyl-dihydropyrroles, which were assumed to be the first-formed intermediates, turn out to be stable entities which have been isolated for the first time. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.097
• 作为产物：
  描述：

  N-Ts-甘氨酸乙酯 、 1-phenyldec-1-yn-3-one 在 tin(ll) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,3S)-3-Hydroxy-3-phenylethynyl-2-(toluene-4-sulfonylamino)-decanoic acid ethyl ester
  参考文献：
  名称：

  A general approach to polysubstituted pyrroles

  摘要：

  Exposure of a range of 3-hydroxy-2-sulfonylamino-4-alkynes to excess iodine delivers good yields of a series of iodopyrroles. Unexpectedly, the hydroxyl-dihydropyrroles, which were assumed to be the first-formed intermediates, turn out to be stable entities which have been isolated for the first time. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.097

文献信息

• A stereoselective synthesis of anti-γ,δ-alkynyl- and -alkenyl-β-hydroxy-α-amino esters from tin(<scp>ii</scp>) enolates of glycinate
  作者：Jonathan J. Gridley、Michael P. Coogan、David W. Knight、K. M. Abdul Malik、Christopher M. Sharland、Jirada Singkhonrat、Siân Williams

  DOI：10.1039/b306291k

  日期：——

  Condensations between the tin(II) enolate 11 of ethyl N-tosylglycinate and conjugated ynals 12 and ynones 14 are highly diastereoselective, in favour of the anti-isomers 13 and 15; similar reactions of enals and enones 17 show lower but still useful levels of anti-stereoselectivity.

  乙基N-对甲苯磺酰甘氨酸盐的锡(II)烯醇化物11与共轭炔醛12和炔酮14之间的缩合反应具有高度的非对映选择性，有利于反式异构体13和15的生成；类似的烯醛和烯酮17反应也表现出较低但仍然有用的反式立体选择性。