(S)-2-tert-butoxycarbonylamino-1,1-diphenylpropane-1,3-diol | 170937-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (S)-2-tert-butoxycarbonylamino-1,1-diphenylpropane-1,3-diol
• CAS: 170937-77-6
• 化学式: C₂₀H₂₅NO₄
• 分子量: 343.423
• InChiKey: NDGXJUPLFIMFJM-KRWDZBQOSA-N

物化性质

• 熔点：
  123 °C
• 沸点：
  548.2±50.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  78.79
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-butoxycarbonylamino-1,1-diphenylpropane-1,3-diol 在 chromium(VI) oxide 、 硫酸 作用下， 以 丙酮 为溶剂， 反应 3.0h， 以51%的产率得到(R)-2-tert-Butoxycarbonylamino-3-hydroxy-3,3-diphenyl-propionic acid
  参考文献：
  名称：

  Stereocontrolled Conversion of L-Serine into a Series of Valuable Unnatural α-Amino Acids

  摘要：

  DOI：

  10.1016/00404-0399(50)1029h-
• 作为产物：
  描述：

  苯基溴化镁 在 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (S)-2-tert-butoxycarbonylamino-1,1-diphenylpropane-1,3-diol
  参考文献：
  名称：

  用于硝基甲烷与靛红的对映选择性硝基-羟醛反应的杂化型方酰胺稠合氨基醇有机催化剂

  摘要：

  合成了一系列杂化型方酸酰胺稠合氨基醇（SFAA）催化剂，并描述了它们在各种靛红与硝基甲烷的对映选择性硝基-羟醛反应中的催化效率。这种转化以优异的化学产率（高达 99 %）和高对映选择性（高达 95 % ee）提供了手性 3-取代 3-羟基吲哚。所得的手性 3-羟基吲哚可进一步用作合成前体，用于合成多种具有广谱迷人生物活性的天然产物。

  DOI：

  10.1002/ejoc.201700138

文献信息

• A Diamino Alcohol Catalyzed Enantioselective Crossed Aldol Reaction of Acetaldehyde with Isatins - A Concise Total Synthesis of Antitumor Agents
  作者：Ummareddy Venkata Subba Reddy、Madhu Chennapuram、Kento Seki、Chigusa Seki、Bheemreddy Anusha、Eunsang Kwon、Yuko Okuyama、Koji Uwai、Michio Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1002/ejoc.201700399

  日期：2017.7.17

  metal-free total syntheses of antitumor and antiviral agents with the tryptanthrin architecture, that is, phaitanthrin B and cephalanthrin A, along with the biologically active indolidine alkaloids chimonamidine and donaxaridine as well as the formal synthesis of CPC-1. The highly enantioselective outcome of this catalytic crossed aldol reaction was evaluated by calculating the Gibbs free energies of the possible

  已使用一系列简单的二氨基醇催化剂开发了靛红衍生物和乙醛的对映选择性交叉羟醛缩合反应，以高化学收率（高达95％）和光学纯度（高达92％）提供了3-取代的3-羟基吲哚-2-酮。  ee）。本方案的合成潜力已通过具有锥虫素结构的抗肿瘤药和抗病毒药的简明，对映体选择性，无保护基团和无过渡金属的总合成得到了证明，这就是类泛素B和脑啡肽A以及具有生物活性的吲哚啶生物碱，mon胺和多那西啶以及CPC-1的正式合成。通过计算可能的过渡态的吉布斯自由能，评估了该催化的交叉羟醛反应的高度对映选择性。
• Thiourea fused γ-amino alcohol organocatalysts for asymmetric Mannich reaction of β-keto active methylene compounds with imines
  作者：Miku Nomura、Zubeda Begum、Chigusa Seki、Yuko Okuyama、Eunsang Kwon、Koji Uwai、Michio Tokiwa、Suguru Tokiwa、Mitsuhiro Takeshita、Hiroto Nakano

  DOI：10.1039/d2ra08317e

  日期：——

  asymmetric Mannich reaction of β-keto active methylene compounds with imines to afford chiral Mannich products, β-amino keto compounds, with continuous chiral centers, that are versatile synthetic intermediates for deriving various biologically active compounds. In particular, the thiourea fused γ-amino alcohols showed satisfactory catalytic activity in this reaction and afforded chiral Mannich products

  在β-酮活性亚甲基化合物与亚胺的不对称曼尼希反应中检查了新型光学活性硫脲稠合γ-氨基醇的催化功能，以提供手性曼尼希产物，β-氨基酮化合物，具有连续手性中心，是通用的合成中间体用于衍生各种生物活性化合物。特别是，硫脲稠合的γ-氨基醇在此反应中表现出令人满意的催化活性，并以优异的化学产率（高达88%）和立体选择性（高达syn : anti /93 : 7 dr，高达99%）提供手性曼尼希产物。 ee）。
• Synthesis of chiral C/N-functionalized morpholine alcohols: study of their catalytic ability as ligand in asymmetric diethylzinc addition to aldehyde
  作者：Rajesh Dave、N. André Sasaki

  DOI：10.1016/j.tetasy.2005.12.027

  日期：2006.2

  A broad variety of chiral C/N-functionalized morpholine alcohols sharing a common structural motif in the 3-(hydroxy-methyl)morpholine 6 were prepared froin criantiomerically pure serine for the purpose of studying their catalytic ligand properties. The asymmetric addition of diethylzinc to benzaldehyde in the presence of 10 mol % of chiral C/N-functionalized morpholine alcohols gave 1-phenyl-1-propanol in 59-81% yield with 10-30% ee. The addition of 10 mol % of n-butyl lithium to the reaction mixture resulted in a significant enhancement of the stereoselectivity in the case of ligands bearing the two geminal phenyl substituents on the backbone. In the presence of n-butyl lithium and using (S)-3-(hydroxydiphcnylmethyl)morpholine (S)-19 as the chiral promoter, (S)-1-phenyl-1 -propanol was obtained in 81% yield with 76% ee. The geminal diphenyl-class of morpholine ligands was examined for the diethylzinc addition to four different aldehydes in the presence of n-butyl lithium. (S)-N-Benzyl-3-(hydroxydiphenymethyl)morpholine (S)-27 was found to be most enantioselective in the case of 4-metlioxybenzaldehyde to give (R)-alcohol in 87K yield with 80% ee. Catalysts (S)-19 and its N-methyl derivative (S)-26 gave alcohols with an (S)-absolute configuration while the N-benzylated derivative (S)-27 gave the opposite enantiomeric products. The tentative transition state models to account for the observed product stereoselectivity with morpholine ligands holding the geminal diphenyl group on the beta-amino alcohol segment are proposed. (c) 2006 Elsevier Ltd. All rights reserved.
• Complete reversal of enantioselection using oxazoline-containing Schiff base ligands derived from l-serine in enantioselective addition of diketene to aldehydes
  作者：Changhu Chu、Koji Morishita、Takanori Tanaka、Masahiko Hayashi

  DOI：10.1016/j.tetasy.2006.09.026

  日期：2006.10

  Starting from one stereogenic center (in this case from L-serine), we obtained two chiral Schiff bases possessing oxazoline moieties, each of which recognized a different enantioface of aldehydes with a high enantionteric excess [up to 93% ee (R) and 89% ee (S)] in the addition reaction of diketene to 2-furfural. (c) 2006 Elsevier Ltd. All rights reserved.