(2R,3R)-5-[2-(benzyloxy)ethyl]-2,3-epoxy-5-en-1-hexanol | 208658-85-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2R,3R)-5-[2-(benzyloxy)ethyl]-2,3-epoxy-5-en-1-hexanol
• 英文别名: [(2R,3R)-3-(2-methylidene-4-phenylmethoxybutyl)oxiran-2-yl]methanol
• CAS: 208658-85-9
• 化学式: C₁₅H₂₀O₃
• 分子量: 248.322
• InChiKey: CAECXHIHADHOSP-HUUCEWRRSA-N

物化性质

• 沸点：
  370.4±22.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R,3R)-5-[2-(benzyloxy)ethyl]-2,3-epoxy-5-en-1-hexanol 在 N-氯代丁二酰亚胺 、 草酰氯 、 二甲基硫 、 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 、 lithium methanolate 、 双氧水 、 甲铝双(2,6-二叔丁基-4-苯甲醚) 、 二甲基亚砜 、 红铝 作用下， 以 甲醇 为溶剂， 生成 [2-[(3R,5R)-3,5-二[[(叔丁基)二甲基硅烷基]氧基]环己基亚基]乙基]二苯基氧膦
  参考文献：
  名称：

  Asymmetric synthesis of a key ring A synthon for 1α-hydroxy-19-nor vitamin D

  摘要：

  A diasteroselective carbonyl ene reaction on a substrate obtained from a regioselective propiolate ene reaction is described for the synthesis of 19-nor A-ring synthon 3. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00682-0
• 作为产物：
  描述：

  (((3-methylbut-3-en-1-yl)oxy)methyl)benzene 在 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 4 A molecular sieve 、 二氯乙基铝 、 二异丁基氢化铝 、 (-)-diethyl tartrate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 (2R,3R)-5-[2-(benzyloxy)ethyl]-2,3-epoxy-5-en-1-hexanol
  参考文献：
  名称：

  具有明显反式激活活性的维生素D杂合类似物的a环合成中的“对称性”：区域选择性丙酸酯-烯，催化对映体选择性环氧化和羰基-烯环化反应的组合序列

  摘要：

  区域选择性丙酸酯-烯反应，催化对映体选择性环氧化和催化对映体选择性羰基-烯环化的结合完成了杂化的19-nor-22-oxa D 3类似物A环的合成（1），显示了在反式激活。

  DOI：

  10.1016/s0040-4039(98)00272-x

文献信息

• “Symmetry” in the synthesis of the a-ring of a vitamin D hybrid analogue with significant transactivation activity: A combinatorial sequence of regioselective propiolate-ene, catalytic enantioselective epoxidation and carbonyl-ene cyclization reactions
  作者：Koichi Mikami、Ayako Osawa、Akira Isaka、Eiji Sawa、Masaki Shimizu、Masahiro Terada、Noboru Kubodera、Kimie Nakagawa、Naoko Tsugawa、Toshio Okano

  DOI：10.1016/s0040-4039(98)00272-x

  日期：1998.5

  The combination of the regioselective propiolate-ene reaction, catalytic enantioselective epoxidation and catalytic enantioselective carbonyl-ene cyclization completes the synthesis of the A ring of the hybrid 19-nor-22-oxa D3 analogue (1), which shows the significant activity in transactivation.

  区域选择性丙酸酯-烯反应，催化对映体选择性环氧化和催化对映体选择性羰基-烯环化的结合完成了杂化的19-nor-22-oxa D 3类似物A环的合成（1），显示了在反式激活。
• Asymmetric synthesis of a key ring A synthon for 1α-hydroxy-19-nor vitamin D
  作者：Lawrence F. Courtney、Meinolf Lange、Milan R. Uskoković、Peter M. Wovkulich

  DOI：10.1016/s0040-4039(98)00682-0

  日期：1998.5

  A diasteroselective carbonyl ene reaction on a substrate obtained from a regioselective propiolate ene reaction is described for the synthesis of 19-nor A-ring synthon 3. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Catalytic asymmetric synthesis and anticancer effects of the novel non-calcemic analog of vitamin D, 2α-fluoro-19-nor-22-oxa-1α,25-dihydroxyvitamin D3 in metastatic lung carcinoma
  作者：Kimie Nakagawa、Toshio Okano、Keiichi Ozono、Shigeaki Kato、Noboru Kubodera、Shiho Ohba、Yoshimitsu Itoh、Koichi Mikami

  DOI：10.1016/j.jfluchem.2007.03.002

  日期：2007.6

  1 alpha,25-Dihydroxyvitamin D-3 (1 alpha,25-D-3) has potent antiproliferative and anti-invasive properties in vitro in cancer cells. However, the major limitation to its clinical use is that it causes hypercalcemia. Therefore, vitamin D analogs with potent cell regulatory effects but with weaker calcemic effects than 1 alpha,25-D-3 are required. Among them, 22-oxa-1 alpha,25-D-3 and 19-nor-1 alpha,25-D-3 have anti-cancer effects with relatively low calcemic effects. Modifications at the C-2ot position of the A-ring also produced analogs with a unique biological profile. Not only the side-chain but also the A-ring modification thus generates a unique analog with potent cell regulatory effects and low calcemic activity as well. We report here that the hybrid 1 alpha,25-D-3 analog, synthesized via the highly regio- and stereo-selective ring opening 2 alpha-fluorination and catalytic asymmetric carbonyl-ene cyclization, with 2 alpha-fluoro, 19-nor, and 22-oxa modification exhibits unique cell regulatory activities against the development of metastatic lung carcinoma. (c) 2007 Published by Elsevier B.V.