tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 123751-09-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• 英文别名: (R)-tert-Butyl 4-(3-methoxy-3-oxoprop-1-en-1-yl)-2,2-dimethyloxazolidine-3-carboxylate；tert-butyl (4R)-4-[(E)-3-methoxy-3-oxoprop-1-enyl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 123751-09-7
• 化学式: C₁₄H₂₃NO₅
• 分子量: 285.34
• InChiKey: YSNYRLFAMVTFTM-QROSGCPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 吡啶 、 锂硼氢 、 三氯化铝 、 碘 、 sodium methylate 、 对甲苯磺酸 、 magnesium 、 三氟乙酸 、 间苯二酚 作用下， 以 四氢呋喃 、 吡啶 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 45.0h， 生成 (3R,4R)-4-(2-hydroxyethyl)-3-(hydroxymethyl)-7-methyl-3,4-dihydro-2H-isoquinolin-1-one
  参考文献：
  名称：

  From serine to functionalized enantiopure tetrahydroisoquinolines

  摘要：

  The reaction of gamma-amino-alpha,beta-unsaturated esters prepared from L-serine with diversely substituted arylcuprates affords the corresponding syn-adducts. Transformation of the amino group to an isocyanate, followed by Friedel-Crafts intramolecular condensation, leads to enantiopure 3,4-disubstituted tetrahydroisoquinolin-1-ones, which can be reduced to the corresponding tetrahydroisoquinolines. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00765-6
• 作为产物：
  描述：

  (R)-4-羟基甲基-2,2-二甲基噁唑啉-3-羧酸叔丁酯 在 戴斯-马丁氧化剂 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  参考文献：
  名称：

  Photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one: A new route to 4(S), 5(S)-disubstituted pyrrolidin-2-ones

  摘要：

  We describe the photoinduced addition of methanol to 5(S)-5-triisopropylsiloxymethyl-N-boc-dihydropyrrole-2(5H)-one to produce 5(S)-triisopropylsiloxymethyl-4( S)-hydroxymethylpyrrolidine-2-one, and conversion of this into a variety of 4( S), S(S)-pyrrolidine-2-ones. Photoinduced addition of methanol to 5(R)-N-boc-5-amino-dihydropyran-2(5H)-one yielded the unexpected product 4(S)-1'-[2'-hydroxy, 1'-( R)-N-boc-amino]ethyl-tetrahydrofuran-2-one via rearrangement of the initial photoadduct. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)01094-1

文献信息

• [EN] AMINOCYCLOHEXANES AND AMINOTETRAHYDROPYRANS AND RELATED COMPOUNDS AS GAMMA-SECRETASE MODULATORS<br/>[FR] AMINOCYCLOHEXANES ET AMINOTÉTRAHYDROPYRANES ET COMPOSÉS ASSOCIÉS COMME MODULATEURS DE GAMMA-SÉCRÉTASE
  申请人：PFIZER

  公开号：WO2011092611A1

  公开（公告）日：2011-08-04

  Compounds and pharmaceutically acceptable salts of the compounds are disclosed, wherein the compounds have the structure of Formula (I) as defined in the specification. Corresponding pharmaceutical compositions, methods of treatment, methods of synthesis, and intermediates are also disclosed.

  本发明揭示了化合物及其在规范中定义的结构为式（I）的药学上可接受的盐。同时还公开了相应的药物组合物、治疗方法、合成方法和中间体。
• On the Stereochemical Divergence in the Conjugate Addition of Lithium Dimethylcuprate/Trimethylsilyl Chloride to γ-Alkoxy and γ-Ureido α,β-Unsaturated Esters
  作者：Stephen Hanessian、Kenzo Sumi

  DOI：10.1055/s-1991-28396

  日期：——

  A comparative study was made of the reaction of chiral non-racemic γ-alkoxy and γ-ureido-α,β-unsaturated esters with lithium dimethylcuprate in the presence of trimethylsilyl chloride. The possible origins of the anti- and syn-additions respectively are discussed and rationalized.

  在三甲基氯硅烷存在下，对手性非气相δ-烷氧基和δ-脲基δ,δ-不饱和酯与二甲基杯酸锂的反应进行了比较研究。分别讨论了反加成和合成加成的可能起源，并使之合理化。
• Total Synthesis of Covalent Cysteine Protease Inhibitor <i>N</i>-Desmethyl Thalassospiramide C and Crystallographic Evidence for Its Mode of Action
  作者：Jeremy Fournier、Karen Chen、Artur K. Mailyan、Jeffrey J. Jackson、Brad O. Buckman、Kumar Emayan、Shendong Yuan、Ravi Rajagopalan、Shawn Misialek、Marc Adler、Michael Blaesse、Andreas Griessner、Armen Zakarian

  DOI：10.1021/acs.orglett.8b03821

  日期：2019.1.18

  A total synthesis of N-desmethyl thalassospiramide C, a unique strained macrocyclic proteobacterial depsipeptide, enabled a detailed crystallographic study of its covalent complex with cathepsin K, a member of a medicinally important family of cysteine proteases. The study provides support for the mechanism of action, and the insight gained can be used for structure-based drug design targeting these

  N-脱甲基海藻螺酰胺C（一种独特的应变大环蛋白杆菌depsipeptide肽）的全合成能够对其与组织蛋白酶K（一种具有重要医学意义的半胱氨酸蛋白酶的成员）的共价复合物进行详细的晶体学研究。该研究为作用机理提供了支持，获得的见解可用于针对这些钙蛋白酶的基于结构的药物设计。
• Intramolecular carbolithiation reactions for the preparation of 3-alkenylpyrrolidines
  作者：Iain Coldham、Kathy N. Price、Richard E. Rathmell

  DOI：10.1039/b303670g

  日期：——

  Tin–lithium exchange allows the formation of α-amino-organolithium species that undergo anionic cyclization onto allylic ethers to give 3-alkenylpyrrolidines. The methodology has been applied to the synthesis of an advanced intermediate related to the natural product (–)-α-kainic acid.

  通过锡锂交换可以形成α-氨基有机锂，这些α-氨基有机锂在烯丙基醚上进行阴离子环化，从而得到 3-烯丙基吡咯烷。该方法已应用于合成与天然产物 (-)-α 卡因酸有关的高级中间体。
• Manganese dioxide can oxidise unactivated alcohols under in situ oxidation–Wittig conditions
  作者：Leonie Blackburn、Xudong Wei、Richard J. K. Taylor

  DOI：10.1039/a903980e

  日期：——

  The in situ alcohol oxidation–Wittig reaction using manganese dioxide as the oxidant has been applied to semi-activated and, for the first time, unactivated alcohols to furnish the corresponding α,β-unsaturated esters.

  以二氧化锰为氧化剂的原位醇氧化-维蒂希反应已应用于半活化醇，并首次应用于未活化醇，以生成相应的δ,δ-不饱和酯。