dimethyl 2-oxo-5-phenylpentanephosphonate | 41640-05-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: dimethyl 2-oxo-5-phenylpentanephosphonate
• 英文别名: dimethyl 2-oxo-5-phenylpentyl phosphonate；Dimethyl (2-oxo-5-phenylpentyl)phosphonate；1-dimethoxyphosphoryl-5-phenylpentan-2-one
• CAS: 41640-05-5
• 化学式: C₁₃H₁₉O₄P
• 分子量: 270.265
• InChiKey: ZVTZGGAWAWFQOO-UHFFFAOYSA-N

物化性质

• 沸点：
  393.0±35.0 °C(Predicted)
• 密度：
  1.131±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  dimethyl 2-oxo-5-phenylpentanephosphonate 在 sodium tetrahydroborate 、 lithium hydroxide monohydrate 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙二醇二甲醚 为溶剂， 反应 7.0h， 生成 (Z)-7-(3,5-dihydroxy-2-[(E)-3-hydroxy-6-phenylhex-1-enyl]cyclopentyl)hept-5-enoic acid
  参考文献：
  名称：

  Harikrishna; Mohan, H. Rama; Dubey, Asian Journal of Chemistry, 2011, vol. 23, # 7, p. 3121 - 3126

  摘要：

  DOI：
• 作为产物：
  描述：

  5-苯基戊烷-2-酮 在 溴 、 sodium iodide 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 反应 9.0h， 生成 dimethyl 2-oxo-5-phenylpentanephosphonate
  参考文献：
  名称：

  Synthesis of (±)-Bimatoprost

  摘要：

  A general synthetic approach has been developed for the synthesis of a key intermediate (6) that can be elaborated into several ophthalmic prostaglandins and their derivatives. Using these strategy, we have obtained (+/-)-bimatoprost (1) and its analog, (+/-)-homobimatoprost (5).

  DOI：

  10.1080/00397911.2010.539754

文献信息

• Stereoselective Synthesis of Functionalized α-Amino Acids Isolated by Filtration
  作者：Ivan Sivák、Michal Toběrný、Andrea Kyselicová、Ol’ga Caletková、Dušan Berkeš、Pavol Jakubec、Andrej Kolarovič

  DOI：10.1021/acs.joc.8b02647

  日期：2018.12.21

  synthetic tool. Despite its numerous advantages, it remains rather rarely used due to its uncertain predictability to occur. Herein, we describe CIDT based on aza-Michael reactions of diversely functionalized (E)-3-acylacrylic acids. This method provides direct access to a broad variety of α-amino acid derivatives in excellent stereochemical purities.

  结晶诱导的非对映异构体转化（CIDT）代表了一种非常有吸引力且方便的合成工具。尽管具有许多优点，但由于不确定的可预测性，因此仍然很少使用。在本文中，我们描述了基于不同功能化（E）-3-酰基丙烯酸的氮杂-迈克尔反应的CIDT 。这种方法可以以优异的立体化学纯度直接获得各种α-氨基酸衍生物。
• Biocatalytic syntheses of chiral non-racemic 2-hydroxyalkanephosphonates
  作者：Remigiusz Żurawiński、Kaoru Nakamura、Józef Drabowicz、Piotr Kiełbasiński、Marian Mikołajczyk

  DOI：10.1016/s0957-4166(01)00567-5

  日期：2001.12

  A series of 2-oxoalkanephosphonates 2 were screened for reduction with Geotrichum candidum. Only diethyl 2-oxopropanephosphonate 2a underwent asymmetric reduction to give (+)-(R)-diethyl 2-hydroxypropanephosphonate 3a with 98% e.e. In turn, a series of racemic 2-hydroxyalkanephosphonates 3 were acetylated under kinetic resolution conditions in the presence of various lipases to give the corresponding 2-acetoxyalkanephosphonates 4 and recovered alcohols 3 in good yields and with e.e. up to 93%. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of (±)-Bimatoprost
  作者：M. Harikrishna、H. Rama Mohan、P. K. Dubey、M. Shankar、Gottumukkala V. Subbaraju

  DOI：10.1080/00397911.2010.539754

  日期：2012.5.1

  A general synthetic approach has been developed for the synthesis of a key intermediate (6) that can be elaborated into several ophthalmic prostaglandins and their derivatives. Using these strategy, we have obtained (+/-)-bimatoprost (1) and its analog, (+/-)-homobimatoprost (5).
• Harikrishna; Mohan, H. Rama; Dubey, Asian Journal of Chemistry, 2011, vol. 23, # 7, p. 3121 - 3126
  作者：Harikrishna、Mohan, H. Rama、Dubey、Shankar、Subbaraju, Gottumukkala V.

  DOI：——

  日期：——