2-(L)-menthyl-dinaphtho[2,1-d:1’,2’-f][1,3,2]dioxaphosphepin-2-sulfide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(L)-menthyl-dinaphtho[2,1-d:1’,2’-f][1,3,2]dioxaphosphepin-2-sulfide
• 英文别名: 13-[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl]oxy-13-sulfido-12,14-dioxa-13-phosphoniapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaene
• 化学式: C₃₀H₃₁O₃PS
• 分子量: 502.614
• InChiKey: XIJMFSJKDLXLNR-FPUALCIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.9
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  28.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  四丁基氟化铵 、 2-(L)-menthyl-dinaphtho[2,1-d:1’,2’-f][1,3,2]dioxaphosphepin-2-sulfide 以 四氢呋喃 为溶剂， 反应 5.5h， 以88%的产率得到(Sp)-N,N,N-tributyl-1-butanaminium (L)-menthylphosphorofluoridothioate
  参考文献：
  名称：

  通过轴-中心手性转移，将具有联萘基的硫代磷酸酯进行氟化水解，导致形成P-手性硫代磷酸一氟盐。

  摘要：

  P-手性硫代磷酸一氟铵盐的不对称合成是通过使用具有双萘基的硫代磷酸O-酯通过轴对中心手性转移反应实现的，盐的绝对立体化学通过X射线分析和比较他们的CD光谱。

  DOI：

  10.1039/c4cc05198j
• 作为产物：
  描述：

  4-((1R,2S,5R)-2-Isopropyl-5-methyl-cyclohexyloxy)-3,5-dioxa-4-phospha-cyclohepta[2,1-a;3,4-a']dinaphthalene 在 1,2,3,4,5,6,7,8-八硫杂环辛烷 作用下， 生成 2-(L)-menthyl-dinaphtho[2,1-d:1’,2’-f][1,3,2]dioxaphosphepin-2-sulfide
  参考文献：
  名称：

  On the use of seven-membered phosphorous heterocycles based on 2,2′-dihydroxy-1,1′-binaphthalene and 1,4∶3,6-dianhydro-d-mannitol in the31P NMR analysis of the enantiomeric composition of chiral alcohols

  摘要：

  Some aspects of phosphorylation of 2,2'-dihydroxy-1,1'-binaphthalene (BINOL) and 1,4:3,6-dianhydro-D-mannitol (isomannide) were investigated. The possibility of using the corresponding cyclic chloro-and amidophosphites for the analysis of enantiomeric compositions of chiral primary and secondary alcohols by P-31 NMR was examined.

  DOI：

  10.1007/bf02495644

文献信息

• Fluorinative hydrolysis of phosphorothioic acid esters with a binaphthyl group through axis-to-center chirality transfer leading to the formation of P-chiral phosphorothioic monofluoridic acid salts
  作者：Toshiaki Murai、Takae Hayashi、Kyohei Yamada、Yuuki Maekawa、Mao Minoura

  DOI：10.1039/c4cc05198j

  日期：——

  Asymmetric synthesis of P-chiral phosphorothioic monofluoridic acid ammonium salts was achieved via axis-to-center chirality transfer reactions by using phosphorothioic acid O-esters with a binaphthyl group, and the absolute stereochemistry of the salts was determined by X-ray analyses and by comparison of their CD spectra.

  P-手性硫代磷酸一氟铵盐的不对称合成是通过使用具有双萘基的硫代磷酸O-酯通过轴对中心手性转移反应实现的，盐的绝对立体化学通过X射线分析和比较他们的CD光谱。
• On the use of seven-membered phosphorous heterocycles based on 2,2′-dihydroxy-1,1′-binaphthalene and 1,4∶3,6-dianhydro-d-mannitol in the31P NMR analysis of the enantiomeric composition of chiral alcohols
  作者：A. A. Bredikhin、Z. A. Bredikhina、F. F. Nigmatzyanov

  DOI：10.1007/bf02495644

  日期：1998.3

  Some aspects of phosphorylation of 2,2'-dihydroxy-1,1'-binaphthalene (BINOL) and 1,4:3,6-dianhydro-D-mannitol (isomannide) were investigated. The possibility of using the corresponding cyclic chloro-and amidophosphites for the analysis of enantiomeric compositions of chiral primary and secondary alcohols by P-31 NMR was examined.