(S)-6-phenylhexane-1,2-diol | 90145-12-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-6-phenylhexane-1,2-diol
• 英文别名: (2S)-6-phenylhexane-1,2-diol
• CAS: 90145-12-3
• 化学式: C₁₂H₁₈O₂
• 分子量: 194.274
• InChiKey: CGWFQTZOKGRZEE-LBPRGKRZSA-N

物化性质

• 沸点：
  343.8±30.0 °C(Predicted)
• 密度：
  1.057±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-6-phenylhexane-1,2-diol 在 咪唑 、 4-二甲氨基吡啶 、 copper(l) iodide 、 (S,S)-[N,N-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexane-diamino]cobalt(III) acetate 、 potassium carbonate 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 生成 (2R,4R)-4-(tert-butyldimethylsilyloxy)-8-phenyloctane-1,2-diol
  参考文献：
  名称：

  First stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one

  摘要：

  A stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one is reported. The strategy utilizes an iterative Jacobsen hydrolytic kinetic resolution, ring opening with a chiral propargylic synthon and a preferential (Z)-Wittig olefination reaction and lactonization as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.056
• 作为产物：
  描述：

  6-苯基-1-己烯 在 (R,R)-(salen)Co(III)(OAc) 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 水 为溶剂， 生成 (S)-6-phenylhexane-1,2-diol
  参考文献：
  名称：

  First stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one

  摘要：

  A stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one is reported. The strategy utilizes an iterative Jacobsen hydrolytic kinetic resolution, ring opening with a chiral propargylic synthon and a preferential (Z)-Wittig olefination reaction and lactonization as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.056

文献信息

• Stereoselective synthesis of (6S) and (6R)-5,6-dihydro-6-[(2R)-2-hydroxy-6-phenylhexyl]-2H-pyran-2-one and their cytotoxic activity against cancer cell lines
  作者：Manchala Narasimhulu、Arepalli Sai Krishna、Janapala Venkateswara Rao、Yenamandra Venkateswarlu

  DOI：10.1016/j.tet.2009.01.101

  日期：2009.4

  Stereoselective total synthesis of α,β-unsaturated lactone (1a), isolated from Ravensara crassifolia, has been achieved efficiently starting from chiral 2,3-O-isopropylidene-d-glyceraldehyde (3) followed by asymmetric allylation and ring-closing metathesis. The antiproliferative activities of compounds 1a, 1b and the unusual bicyclic compound 2 were evaluated against three-cancer cell lines, THP-1

  α的立体选择性全合成，β不饱和内酯（1A）中，从分离罗文莎云杉，已经实现了有效地从起始手性2,3- ö异亚丙基d甘油醛（3接着不对称烯丙基和闭环复分解）。评估了化合物1a，1b和不寻常的双环化合物2对三种癌细胞系THP-1和U-937（白血病）和A-375（黑色素瘤）的抗增殖活性。
• An azido-functionalized isocarbacyclin analogue acting as an efficient photoaffinity probe for a prostacyclin receptor
  作者：Masaaki Suzuki、Hiroshi Koyano、Ryoji Noyori、Hitoshi Hashimoto、Manabu Negishi、Atsushi Ichikawa、Seiji Ito

  DOI：10.1016/s0040-4020(01)88526-4

  日期：1992.3

  A stable prostacyclin analogue, (15S)-18c, having an azidophenyl, group as a photoaffinity labeling functionality has been synthesized. This compound has a sufficiently high affinity to the prostacyclin receptor protein in mastocytoma P-815 cells, exhibiting an IC50 value of 3 nM for the replacement of iloprost bound to the receptor protein. A photoaffinity probe compound, [H-3]-(15S)-18c, is obtainable by reduction of the ketone 16c with [H-3]NaBH4-CeCl3 followed by alkaline hydrolysis of the methyl ester.
• First stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one
  作者：Palakodety Radha Krishna、Ravula Srinivas

  DOI：10.1016/j.tetlet.2007.01.056

  日期：2007.3

  A stereoselective total synthesis of (6R)-6-[(4R,6R)-4,6-dihydroxy-10-phenyldec-1-enyl]-5,6-dihydro-2H-pyran-2-one is reported. The strategy utilizes an iterative Jacobsen hydrolytic kinetic resolution, ring opening with a chiral propargylic synthon and a preferential (Z)-Wittig olefination reaction and lactonization as the key steps. (c) 2007 Elsevier Ltd. All rights reserved.