(R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2' diyl hydrogen phosphate | 39648-63-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: (R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2' diyl hydrogen phosphate
• 英文别名: (R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthalene-2,2'-diyl phosphoric acid；(R)-5,5',6,6',7,7',8,8'-Octahydro-1,1'-bi-2-naphthyl phosphate；13-hydroxy-12,14-dioxa-13λ5-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3(8),9,16,18(23)-hexaene 13-oxide
• CAS: 39648-63-0
• 化学式: C₂₀H₂₁O₄P
• 分子量: 356.358
• InChiKey: HCTOYKLUBVCMFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2' diyl hydrogen phosphate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(R)-5,5',6,6',7,7',8,8'-八氢-[1,1'-联萘]-2,2'-二酚
  参考文献：
  名称：

  Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations

  摘要：

  A direct single-step hydrogenation of BINOL-based chiral phosphoric acids, N-triflyl phosphoramides, and disulfonimides to the corresponding H8-BINOL Bronsted acids in excellent yields and chemoselectivities is described. In addition, the conditions for the single-step oxidation of H8-BINOL-based Bronsted acids into the corresponding BINOL-based acids have been identified and employed to accomplish these interconversions in 41-81% yield.

  DOI：

  10.1021/acs.orglett.5b01754
• 作为产物：
  描述：

  S-联萘酚磷酸酯 在 二氧化铂 、 氢气 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 16.0h， 以98%的产率得到(R)-5,5',6,6',7,7',8,8'-octahydro-1,1'-binaphthyl-2,2' diyl hydrogen phosphate
  参考文献：
  名称：

  Direct Interconversion of BINOL and H8-BINOL-Based Chiral Brønsted Acids Using Single-Step Red/Ox Manipulations

  摘要：

  A direct single-step hydrogenation of BINOL-based chiral phosphoric acids, N-triflyl phosphoramides, and disulfonimides to the corresponding H8-BINOL Bronsted acids in excellent yields and chemoselectivities is described. In addition, the conditions for the single-step oxidation of H8-BINOL-based Bronsted acids into the corresponding BINOL-based acids have been identified and employed to accomplish these interconversions in 41-81% yield.

  DOI：

  10.1021/acs.orglett.5b01754

文献信息

• Facile and Efficient Enantioselective Strecker Reaction of Ketimines by Chiral Sodium Phosphate
  作者：Ke Shen、Xiaohua Liu、Yunfei Cai、Lili Lin、Xiaoming Feng

  DOI：10.1002/chem.200900210

  日期：2009.6.8

  Asymmetric catalysis: A facile enantioselective Strecker reaction of ketimines with trimethylsilyl cyanide (TMSCN) was realized by employing chiral (S)‐BNPNa 3 e and PBAP as an additive (see image). A wide substrate scope and good‐to‐excellent enantioselectivities were achieved.

  不对称催化：一种简便的对映选择性的Strecker用氰化三甲基硅烷（TMSCN）酮亚胺的反应，通过采用手性（实现小号）-BNPNa图3e和PBAP作为添加剂（见图像）。获得了较宽的底物范围和出色的对映选择性。
• [EN] APPLICATION OF BIPHENYL PHOSPHATE COMPOUND AS GPR84 ANTAGONIST<br/>[FR] APPLICATION DE COMPOSÉ DE PHOSPHATE DE BIPHÉNYLE EN TANT QU'ANTAGONISTE DE GPR84<br/>[ZH] 联苯磷酸酯类化合物作为GPR84拮抗剂的应用
  申请人：SHANGHAI INST MATERIA MEDICA CAS

  公开号：WO2020007342A1

  公开（公告）日：2020-01-09

  一种联苯磷酸酯类化合物的应用，用于制备GPR84拮抗剂；用作GPR84拮抗剂；或用于制备治疗GPR84受体高表达或兴奋性过高所导致的相关疾病的药物，该联苯磷酸酯类化合物的结构如通式I所示，各取代基的定义如说明书和权利要求书所述。联苯磷酸酯类化合物，作为GPR84受体拮抗剂，有望成为可以治疗炎症相关疾病，如多发性硬化症、炎症性肠病、关节炎、肝纤维化、肺纤维化等的新型药物。
• Binaphthol monophosphoric acid derivative and its use
  申请人：Tosoh Corporation

  公开号：EP1038877A1

  公开（公告）日：2000-09-27

  A binaphthol monophosphoric acid derivative of the following formula (1), (2), (3) or (4): wherein each of R1, R2, R3 and R4 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C1-20 linear or branched alkenyl group, a C1-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1-to 4-carbon atom by a C1-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group, provided that R1 to R4 are not simultaneously hydrogen, wherein each of R5, R6, R7 and R8 which are independent of one another, is hydrogen, a C1-20 linear or branched alkyl group, a C1-20 linear or branched alkenyl group, a C1-20 linear or branched alkynyl group, a phenyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkyl group, a phenyl group having its nucleus substituted at the 1- to 4-carbon atom by a C1-10 linear or branched alkenyl group, a phenyl group having its nucleus substituted at the 1-to 4-carbon atom by a C1-10 linear or branched alkynyl group, a naphthyl group or a C3-8 cycloalkyl group.

  下式(1)、(2)、(3)或(4)的二萘酚单磷酸衍生物： 其中相互独立的 R1、R2、R3 和 R4 各为氢、C1-20 直链或支链烷基、C1-20 直链或支链烯基、C1-20 直链或支链炔基、苯基、其核在 1 至 4 碳原子上被 C1-10 直链或支链烷基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链烯基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链炔基取代的苯基、萘基或 C3-8 环烷基，条件是 R1 至 R4 不同时为氢、 其中相互独立的 R5、R6、R7 和 R8 各为氢、C1-20 直链或支链烷基、C1-20 直链或支链烯基、C1-20 直链或支链炔基、苯基、其核在 1-4 碳原子上被 C1-10 直链或支链烷基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链烯基取代的苯基、在 1 至 4 碳原子处其核被 C1-10 直链或支链炔基取代的苯基、萘基或 C3-8 环烷基。
• US6274745B1
  申请人：——

  公开号：US6274745B1

  公开（公告）日：2001-08-14
• US7517828B2
  申请人：——

  公开号：US7517828B2

  公开（公告）日：2009-04-14