N,N'-bis[O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N-methylphosphoramidite]ethylenediamine | 380366-60-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N,N'-bis[O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N-methylphosphoramidite]ethylenediamine
• 英文别名: 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'-dimethylethane-1,2-diamine
• CAS: 380366-60-9；185449-89-2
• 化学式: C₄₄H₃₄N₂O₄P₂
• 分子量: 716.712
• InChiKey: MMZBSYYXUGVYHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  52
• 可旋转键数：
  5
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  59
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate 、 N,N'-bis[O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N-methylphosphoramidite]ethylenediamine 以 not given 为溶剂， 生成 [Rh(COD)(C20H12O2P)2(NCH3)2(CH2)2]BF4
  参考文献：
  名称：

  手性二亚磷酸酯和二亚磷酰胺基化合物在Rh催化的不对称烯烃加氢中作为便宜且有效的配体。

  摘要：

  得自BINOL或二苯基脯氨醇的手性二亚磷酸酯和二亚磷酰胺基化合物是不对称Rh催化的烯烃加氢的有效配体，只要选择合适的非手性骨架即可。

  DOI：

  10.1039/b601638c
• 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， 反应 16.0h， 生成 N,N'-bis[O,O'-(S)-(1,1'-dinaphthyl-2,2'-diyl)-N-methylphosphoramidite]ethylenediamine
  参考文献：
  名称：

  使用铜-亚磷酰胺络合物的二烷基锌试剂的对映选择性催化共轭加成；配体变化和非线性效应

  摘要：

  合成了多种新的手性亚磷酰胺，并在铜催化的对乙基己烯酮和查耳酮的铜催化对映选择性共轭加成中进行了测试，以评估对立体控制至关重要的结构特征。空间要求高的胺部分对于达到高ee是必不可少的。发现查尔酮的对映选择性高达89％，环烯酮的对映选择性高达98％。对具有最佳配体的环己烯酮和查尔酮的非线性效应的研究表明，环状和非环状烯酮均具有明显的非线性效应。

  DOI：

  10.1016/s0040-4020(00)00142-3

文献信息

• Vries, Andre H. M. de; Meetsma, Auke; Feringa, Ben L., Angewandte Chemie, 1996, vol. 108, # 20, p. 2526 - 2528
  作者：Vries, Andre H. M. de、Meetsma, Auke、Feringa, Ben L.

  DOI：——

  日期：——
• 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.
• Enantioselective Catalytic Conjugate Addition of Dialkylzinc Reagents using Copper–Phosphoramidite Complexes; Ligand Variation and Non-linear Effects
  作者：Leggy A Arnold、Rosalinde Imbos、Alessandro Mandoli、André H.M de Vries、Robert Naasz、Ben L Feringa

  DOI：10.1016/s0040-4020(00)00142-3

  日期：2000.4

  cyclohexenone and chalcone in order to assess the structural features that are important for stereocontrol. A sterically demanding amine moiety is essential to reach high e.e.’s. Enantioselectivities for chalcones up to 89% and for cyclic enones up to 98% were found. Studies on non-linear effects with the best ligands for both cyclohexenone and chalcone showed clear non-linear effects for both cyclic

  合成了多种新的手性亚磷酰胺，并在铜催化的对乙基己烯酮和查耳酮的铜催化对映选择性共轭加成中进行了测试，以评估对立体控制至关重要的结构特征。空间要求高的胺部分对于达到高ee是必不可少的。发现查尔酮的对映选择性高达89％，环烯酮的对映选择性高达98％。对具有最佳配体的环己烯酮和查尔酮的非线性效应的研究表明，环状和非环状烯酮均具有明显的非线性效应。
• Chiral diphosphites and diphosphoramidites as cheap and efficient ligands in Rh-catalyzed asymmetric olefin hydrogenation
  作者：Manfred T. Reetz、Gerlinde Mehler、Oleg Bondarev

  DOI：10.1039/b601638c

  日期：——

  Chiral diphosphites and diphosphoramidites derived from BINOL or diphenylprolinol are efficient ligands in asymmetric Rh-catalyzed olefin hydrogenation, provided the proper achiral backbone is chosen.

  得自BINOL或二苯基脯氨醇的手性二亚磷酸酯和二亚磷酰胺基化合物是不对称Rh催化的烯烃加氢的有效配体，只要选择合适的非手性骨架即可。