tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate | 241478-39-7

• 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: tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate
• 英文别名: tert-butyl N-[(E,2S,3R)-1,3-dihydroxydodec-4-en-2-yl]carbamate
• CAS: 241478-39-7
• 化学式: C₁₇H₃₃NO₄
• 分子量: 315.453
• InChiKey: QEJUXXUIIOSOLZ-AMXOMPAFSA-N

物化性质

• 沸点：
  466.0±45.0 °C(Predicted)
• 密度：
  1.014±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate 在 吡啶 、 三甲基溴硅烷 、 四溴化碳 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors

  摘要：

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.001
• 作为产物：
  描述：

  tert-butyl (4S)-4-<(1R)-1-hydroxy-2-decynyl>-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 甲醇 、 Amberlyst 15 、 红铝 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 72.0h， 生成 tert-butyl (1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-undecenylcarbamate
  参考文献：
  名称：

  Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons

  摘要：

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.

  DOI：

  10.1021/jm990091e

文献信息

• Structure-activity relationship of short-chain sphingoid bases as inhibitors of sphingosine kinase
  作者：Steven De Jonghe、Ilse Van Overmeire、Samantha Poulton、Chris Hendrix、Roger Busson、Serge Van Calenbergh、Denis De Keukeleire、Sarah Spiegel、Piet Herdewijn

  DOI：10.1016/s0960-894x(99)00554-5

  日期：1999.11

  Short-chain sphinganine analogues 8, 9, 18, and 19 as well as 3-fluoro-sphingosine analogues 25 and 26 were synthesized. Their potential as sphingosine kinase inhibitors was investigated, in combination with previously synthesized sphingosine and fluorinated sphinganine analogues. (C) 1999 Elsevier Science Ltd. All rights reserved.
• Syntheses of sphingosine-1-phosphate analogues and their interaction with EDG/S1P receptors
  作者：Hyun-Suk Lim、Jeong-Ju Park、Kwangseok Ko、Mee-Hyun Lee、Sung-Kee Chung

  DOI：10.1016/j.bmcl.2004.03.001

  日期：2004.5

  Sphingosine-I-phosphate (SIP) is an important regulator of a wide variety of biological processes acting as an endogenous ligand to EDG/S1P receptors. In an effort to establish structure-activity relationship between EDG/S1P and ligands, we report herein homology modeling study of EDG-1/S1P(1), syntheses of S I P analogues, and cell based binding affinity study for EDG/S1P receptors. (C) 2004 Elsevier Ltd. All rights reserved.
• Effect of Aromatic Short-Chain Analogues of Ceramide on Axonal Growth in Hippocampal Neurons
  作者：Ilse Van Overmeire、Swetlana A. Boldin、Filip Dumont、Serge Van Calenbergh、Guido Slegers、Denis De Keukeleire、Anthony H. Futerman、Piet Herdewijn

  DOI：10.1021/jm990091e

  日期：1999.7.1

  A series of D-erythro- and L-threo-ceramide analogues was synthesized and investigated for their ability to reverse the inhibitory effects of fumonisin B-1 (FB1) on axonal growth in hippocampal neurons. The analogues contained either a C-7 Side chain or a phenyl group substituted for the C-13 residue present in naturally occurring ceramides, while the N-acyl chain length was reduced from C-16-C-24 to C-2-C-8. D-erythro-Ceramide 18a with a C-7 Side chain and an N-acetyl residue and D-erythro-ceramide 20c with an aromatic side chain and an N-hexanoyl residue were most active in reversing the inhibitory effects of FB1 on axonal growth, although the mechanism remains unclear.