(R)-2-methoxy-1,4-butanediol | 130408-40-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-methoxy-1,4-butanediol
• 英文别名: (2R)-2-methoxybutane-1,4-diol
• CAS: 130408-40-1
• 化学式: C₅H₁₂O₃
• 分子量: 120.148
• InChiKey: BWVRAKJOMJIOQX-RXMQYKEDSA-N

物化性质

• 沸点：
  241.0±20.0 °C(Predicted)
• 密度：
  1.064±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  8
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-methoxy-1,4-butanediol 在 盐酸 、 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 正丁胺 、 copper dichloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 22.5h， 生成 (R)-2-methoxy-1,4-butandiyl 5,5'-bis(benzyloxy)-4,4',6,6'-tetrahydroxy-1,1'-biphenyl-2,2'-dicarboxylate
  参考文献：
  名称：

  Synthesis of Chiral and Modifiable Hexahydroxydiphenoyl Compounds

  摘要：

  A reliable method for synthesizing each enantiomer of the hexahydroxydiphenoyl (HHDP) cornpounds has been developed. The synthesis involved atropselective construction of the aryl-aryl bond of the HHDP compounds. This construction relied on the CuCl2.n-BuNH2-mediated intramolecular coupling of bis (4-O-benzyl- gallate) on two simple chiral auxiliaries, both of which were derived from L-(+)-tartaric acid. The coupling reaction realized complete or near-perfect atropselectivity. The two auxiliaries induced opposite axial chirality despite their identical origin. The diastereoselectivities of these couplings were probably controlled kinetically. Modifications of the free phenolic hydroxy groups and the carbonyl groups in the resulting HHDP compounds demonstrated the potential derivatization of a wide variety of HHDP analogues.

  DOI：

  10.1021/jo201750d
• 作为产物：
  描述：

  R-(+)-dimethyl methoxysuccinate 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 以40%的产率得到(R)-2-methoxy-1,4-butanediol
  参考文献：
  名称：

  (+)-Trienomycins A、B、C 和 F 和 (+)-Mycotrienins I 和 II：相对和绝对立体化学

  摘要：

  安沙霉素抗生素 (+)-三烯霉素 A、B 和 C 及其有效的抗真菌同源物 (+)-霉菌三烯素 I 和 II 的完整相对和绝对立体化学已经阐明。一个新物种，(+)-trienomycin F，也已被分离和表征。此外，还开发了三烯霉素和霉菌三烯素的最终合成策略。

  DOI：

  10.1021/ja961400i

文献信息

• (+)-Thiazinotrienomycin E: Relative and absolute stereochemistry
  作者：Amos B Smith、Joseph Barbosa、Nobuo Hosokawa、Hiroshi Naganawa、Tomio Takeuchi

  DOI：10.1016/s0040-4039(98)00426-2

  日期：1998.5

  The complete relative and absolute configurations of (+)-thiazinotrienomycin E, a potent new ansatrienin cancer cell growth inhibitory agent, have been determined via degradation and chemical correlation.

  已通过降解和化学相关性确定了（+）-噻嗪诺米诺霉素E（一种有效的新型ansatrienin癌细胞生长抑制剂）的完整相对和绝对构型。
• Synthesis and in vitro cytotoxicity of novel hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes
  作者：Haibin Zhu、Kai Cui、Lianhong Wang、Shaohua Gou

  DOI：10.1016/j.bmcl.2005.08.025

  日期：2005.11

  Twenty-six new hydrophilic chiral 2-alkoxy-1,4-butanediamine platinum (II) complexes having a seven-membered ring structure between a bidentate carrier ligand and a platinum atom have been synthesized and most of them were evaluated for their in vitro cytotoxicity toward A549 human non-small cell lung carcinoma and HCT-116 human colon cancer cell lines. The cytotoxicities of platinum complexes are related to the nature of the carrier ligand and leaving group. Complex 5'b, viz. cis-dichloro[(2R)ethoxy-1,4-butanediamine] platinum (11), exhibits the greatest potency among those 21 tested platinum complexes in both cell lines. (c) 2005 Elsevier Ltd. All rights reserved.
• (+)-Trienomycins A, B, and C: relative and absolute stereochemistry
  作者：Amos B. Smith、John L. Wood、Weichyun Wong、Alexandra E. Gould、Carmelo J. Rizzo、Shinji Funayama、Satoshi Omura

  DOI：10.1021/ja00176a070

  日期：1990.9
• SMITH, AMOS (III);WOOD, JOHN L.;WONG, WEICHYUN;GOULD, ALEXANDRA E.;RIZZO,+, J. AMER. CHEM. SOC., 112,(1990) N0, C. 7425-7426
  作者：SMITH, AMOS (III)、WOOD, JOHN L.、WONG, WEICHYUN、GOULD, ALEXANDRA E.、RIZZO,+

  DOI：——

  日期：——
• (+)-Trienomycins A, B, C, and F and (+)-Mycotrienins I and II:  Relative and Absolute Stereochemistry
  作者：Amos B. Smith、John L. Wood、Weichyun Wong、Alexandra E. Gould、Carmelo J. Rizzo、Joseph Barbosa、Kanki Komiyama、Satoshi Ōmura

  DOI：10.1021/ja961400i

  日期：1996.1.1

  The complete relative and absolute stereochemistries have been elucidated for the ansamycin antibiotics (+)-trienomycins A, B, and C and their potent antifungal congeners, the (+)-mycotrienins I and II. A new species, (+)-trienomycin F, has also been isolated and characterized. In addition, an end-game synthetic strategy for the trienomycins and mycotrienins has been developed.

  安沙霉素抗生素 (+)-三烯霉素 A、B 和 C 及其有效的抗真菌同源物 (+)-霉菌三烯素 I 和 II 的完整相对和绝对立体化学已经阐明。一个新物种，(+)-trienomycin F，也已被分离和表征。此外，还开发了三烯霉素和霉菌三烯素的最终合成策略。