(-)-8-phenylmenthyl dimethyl phosphonoacetate | 113368-89-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-8-phenylmenthyl dimethyl phosphonoacetate
• 英文别名: [(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl] 2-dimethoxyphosphorylacetate
• CAS: 113368-89-1
• 化学式: C₂₀H₃₁O₅P
• 分子量: 382.437
• InChiKey: ASGMRAURJFEUIO-KBAYOESNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (-)-8-phenylmenthyl dimethyl phosphonoacetate 在 Amberlyst 15 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.5h， 生成 (1R,2S,5R)-8-phenylmenthyl (E)-5-hydroxy-2-pentenoate
  参考文献：
  名称：

  Enantioselective Synthesis of (7R,8R,8aR)- and (7S,8S,8aS)-7-Hydroxy-8-indolizidinemethanol by 1,3-Dipolar Cycloaddition of 1-PyrrolineN-Oxide to Chiral Pentenoates

  摘要：

  DOI：

  10.1002/1099-0690(200011)2000:21<3595::aid-ejoc3595>3.0.co;2-n
• 作为产物：
  描述：

  (-)-8-苯基薄荷醇 生成 (-)-8-phenylmenthyl dimethyl phosphonoacetate
  参考文献：
  名称：

  - or -selective Horner-Wittig reactions of substituted bicyclo[3.3.0]octane-3-ones with chiral phosphonoacetates

  摘要：

  DOI：

  10.1016/s0040-4039(00)82040-7

文献信息

• The influence of chiral auxiliaries and catalysts on the selectivity of intramolecular conjugate additions of pyrrole to N-tethered Michael acceptors
  作者：Martin G. Banwell、Daniel A. S. Beck、Jason A. Smith

  DOI：10.1039/b312552a

  日期：——

  A series of pyrroles incorporating N-tethered acrylates and related groups has been prepared and examined for their capacity to undergo intramolecular Michael addition reactions to form, in a diastereo- or enantio-selective fashion, the corresponding 8-substituted tetrahydroindolizidine or homologues thereof.

  制备了一系列包含N-连接的丙烯酸酯及相关基团的吡咯化合物，并研究了它们进行分子内Michael加成反应的能力，以构象选择性或对映选择性的方式生成相应的8-取代四氢� indolizidine 或其同系物。
• Efficient ester exchange reaction of phosphonoacetates
  作者：Susumi Hatakeyama、Kumiko Satoh、Kuniya Sakurai、Seiichi Takano

  DOI：10.1016/s0040-4039(00)96188-4

  日期：1987.1

  A novel method for the preparation of differentially substituted phosphonoacetates and phosphonoacetamides using 4-DMAP catalyzed ester exchange reaction has been developed.

  已开发出一种使用4-DMAP催化的酯交换反应制备差异取代的膦酰基乙酸酯和膦酰基乙酰胺的新方法。
• Total Synthesis of (+)-3-Oxacarbacyclin 1. Retrosynthesis and Asymmetric Olefination through Horner–Wadsworth–Emmons, Peterson and Martin Reactions
  作者：Hans-Joachim Gais、Gerhard Schmiedl、Rainer K. L. Ossenkamp

  DOI：10.1002/jlac.199719971205

  日期：1997.12

  esters 7a/b serve as starting material for the total synthesis of (+)-3-oxacarbacyclin. Similarly, the reaction of 8b with ent-Li-10a gave the esters ent-7b and ent-11b in a ratio of 95:5 in 82% yield. The olefination of 8b with rac-16 afforded a mixture of the esters rac-17 and rac-18, of yet unassigned configuration, in a ratio of 70:30. The HWE reactions of 8a/b with Li-10a, ent-Li-10a and rac-Li-10b

  前手性酮8a / b与膦酰基乙酸酯10a，ent - 10a，10b和rac - 16的不对称Horner-Wadsworth-Emmons（HWE）反应，其中包含8-苯基薄荷醇，8-苯基去薄荷醇和反式-2-（三苯基甲硅烷基） -环己醇分别作为手性助剂进行了研究。低温下8a与膦酰基烯醇酸酯Li- 10a / b的HWE反应以高收率得到酯7a / b和11a / b，非对映选择性高达97：3。（E）-构型的酯7a / b用作（+）-3-oxacarbacyclin的全合成原料。类似地，8b与ent -Li- 10a的反应以95：5的比例得到ent - 7b和ent - 11b酯，产率为82％。8b与rac - 16的烯烃化反应得到酯rac - 17和rac - 18的混合物，其比例尚未分配，比例为70:30。8a / b与Li- 10a，ent -Li- 10a的HWE反应rac -Li -
• Stereodivergent synthesis of two diastereoisomeric enoates by asymmetric horner–wadsworth–emmons reaction using a single chiral auxiliary
  作者：Toshiaki Furuta、Michiko Iwamura

  DOI：10.1039/c39940002167

  日期：——

  Stereodivergent synthesis of both diastereoisomeric enoates, including vinylogous acids, is achieved in the kinetic resoultion of branched aldehydes and asymmetrization of prochiral cyclic ketone by chiral phosphorus reagents derived from (–)-8-phenylmenthol.

  通过手性磷试剂对支链醛进行动力学复分解和对原手性环酮进行不对称分解，实现了非对映异构烯酸盐（包括乙烯基酸）的立体异构合成。
• A New Candidate for a Properly Substituted CD Ring Component of Vitamin D3 via Intramolecular Asymmetric Olefination of a 1,3-Cyclopentanedione Derivative
  作者：Tadakatsu Mandai、Yuichi Kaihara、Jiro Tsuji

  DOI：10.1021/jo00099a002

  日期：1994.10

  A highly diastereoselective synthesis of hydrindenone derivative 5 (98% de) was achieved via diastereotopic differentiation of 1,3-cyclopentanedione derivative 4 by intramolecular Horner-Emmons olefination. In addition, the compound 5 was converted to ketone 2, a new building block far 1 alpha,25-dihydroxyvitamin D-3 (1).