N,N'-bis{(S)-1,2-dihydro-[2',1'-c:1',2'-e]dinaphtho-2,7-dioxa-7H-phosphepine-1-yl}-N,N'-bis[(S)-(1-phenylethyl)]propylenediamine

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-bis{(S)-1,2-dihydro-[2',1'-c:1',2'-e]dinaphtho-2,7-dioxa-7H-phosphepine-1-yl}-N,N'-bis[(S)-(1-phenylethyl)]propylenediamine
• 英文别名: N,N'-bis{(R)-1,2-dihydro-[2',1'-c:1',2'-e]dinaphtho-2,7-dioxa-7H-phosphepine-1-yl}-N,N'-bis[(S)-(1-phenylethyl)]propylenediamine；N,N'-bis(12,14-dioxa-13-phosphapentacyclo[13.8.0.02,11.03,8.018,23]tricosa-1(15),2(11),3,5,7,9,16,18,20,22-decaen-13-yl)-N,N'-bis[(1S)-1-phenylethyl]propane-1,3-diamine
• 化学式: C₅₉H₄₈N₂O₄P₂
• 分子量: 910.989
• InChiKey: ATCPMZOFMWRYNN-YATWDLPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.1
• 重原子数：
  67
• 可旋转键数：
  10
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  S-1,1'-联-2-萘酚 在 三乙胺 、 三氯化磷 作用下， 以 甲苯 为溶剂， 生成 N,N'-bis{(S)-1,2-dihydro-[2',1'-c:1',2'-e]dinaphtho-2,7-dioxa-7H-phosphepine-1-yl}-N,N'-bis[(S)-(1-phenylethyl)]propylenediamine
  参考文献：
  名称：

  New bidentate chiral phosphoramidites in copper-catalyzed asymmetric 1,4-addition of diethylzinc to cyclic α,β-enones: enantioselective tandem 1,4-addition-aldol reactions with 2-cyclopentenone

  摘要：

  New bidentate phosphoramidites were prepared starting from alpha,alpha,alpha ',alpha ' -tetraphenyl-2,2-dimethyl-1,3-dioxolane-4,5-dimethanol (TADDOL) or 1,1 ' -bi-2-naphthol (BINOL) and either 1,2-ethylene- or 1,3-propylenediamine N,N ' -disubstituted with achiral or chiral groups. The use of these ligands in the copper-catalyzed enantioselective conjugate addition of diethylzinc to 2-cyclohexenone and 2-cyclopentenone afforded products with e.e.s of up to 89 and 83%. respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00348-2

文献信息

• PROCESS FOR THE PREPARATION OF ENANTIOMERICALLY ENRICHED COMPOUNDS
  申请人：MINNAARD Adriaan Jacobus

  公开号：US20080275274A1

  公开（公告）日：2008-11-06

  Process for the preparation of enantiomerically enriched compounds of formula Ar—C(R 1 )—C(R 2 )-Z wherein Ar represents an optionally substituted (hetero)aryl group R 1 and R 2 , each independently, represent H, an alkyl, (hetero)aryl, dialkylamino, amido, thioether, alkoxy or aryloxy group with the proviso that not both R 1 and R 2 represent H, or R 1 and R 2 form together with the C-atoms to which they are bound a (hetero)alkyl or (hetero)alkenyl ring and Z represents an electron withdrawing group, in which process a boronic acid derivate of formula Ar—B(OR 3 )OR 4 or its anhydride, wherein R 3 and R 4 , each independently, represent H or an alkyl group, is reacted with an olefinic unsaturated compound of formula R 2 —C═C—(R 1 )Z in the presence of a transition metal catalyst comprising a transition metal chosen from Cu and group VIII and an enantiomerically enriched ligand L, having formula (I) where C n together with the two O-atoms and the P-atom forms a substituted or nonsubstituted ring with 2-6 C-atoms, R 5 and R 6 each independently represent H, an optionally substituted alkyl, aryl, alkaryl, or aralkyl group, or the group of formula (II) wherein C n 1 may have the same meanings as given for C n and B represents a bridging group, or R 5 and R 6 may form a heterocyclic ring together with the N-atom to which they are bound.