(S)-N-(1-methylethyl)-4-amino-2-butanol | 145124-75-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (S)-N-(1-methylethyl)-4-amino-2-butanol
• 英文别名: (S)-N-Isopropyl-4-aminobutan-2-ol；(S)-1-N-isopropylbutan-2-ol；(2S)-4-(propan-2-ylamino)butan-2-ol
• CAS: 145124-75-0
• 化学式: C₇H₁₇NO
• 分子量: 131.218
• InChiKey: NGVGMMWXUKIWPX-ZETCQYMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-N-(1-methylethyl)-4-amino-2-butanol 在 劳森试剂 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 反应 34.5h， 生成 (S)-(2l,6l)-2-(methoxymethyl)-6-methyl-3-(1-methylethyl)-1,3,2-oxazaphosphorinane 2-sulfide
  参考文献：
  名称：

  Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions

  摘要：

  A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different a-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidates (2-thioxo-1,3,2-oxazaphosphorinanes) underwent smooth electrophilic substitutions with excellent diastereoselectivity for both cis and trans stereoisomers. Highly enantioselective synthesis of alpha-alkoxyphosphonates in either antipodal form can be achieved by the employment of highly diastereoselective alkylation with anions derived from the corresponding P-methoxymethyl analogs in the presence of HMPA or PMDTA. Implications for the aggregation states and reactive conformations of the anions are discussed.

  DOI：

  10.1021/ja00153a009
• 作为产物：
  描述：

  (S)-N-(1-methylethyl)-3-hydroxybutyramide 在 硼烷四氢呋喃络合物 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到(S)-N-(1-methylethyl)-4-amino-2-butanol
  参考文献：
  名称：

  Alkylations of Chiral, Phosphoryl- and Thiophosphoryl-Stabilized Carbanions

  摘要：

  A general method for the preparation of enantiomerically enriched phosphonic acids and phosphonates with three different a-substitution patterns (aryl, alkyl, and alkoxy) has been developed. Anions derived from enantiomerically enriched thiophosphonamidates (2-thioxo-1,3,2-oxazaphosphorinanes) underwent smooth electrophilic substitutions with excellent diastereoselectivity for both cis and trans stereoisomers. Highly enantioselective synthesis of alpha-alkoxyphosphonates in either antipodal form can be achieved by the employment of highly diastereoselective alkylation with anions derived from the corresponding P-methoxymethyl analogs in the presence of HMPA or PMDTA. Implications for the aggregation states and reactive conformations of the anions are discussed.

  DOI：

  10.1021/ja00153a009

文献信息

• Acetamide thienotriazolodiazepines and uses thereof
  申请人：Dana-Farber Cancer Institute, Inc.

  公开号：US10881668B2

  公开（公告）日：2021-01-05

  The present invention provides compounds of Formula (I), and pharmaceutically compositions thereof. Compounds of Formula (I) are binders of bromodomains and/or bromodomain-containing proteins (e.g., bromo and extra terminal (BET) proteins). Also provided are methods, uses, and kits using the compounds and pharmaceutical compositions for inhibiting the activity (e.g., increased activity) of bromodomains and/or bromodomain containing proteins and for treating and/or preventing in a subject diseases associated with bromodomains or bromodomain-containing proteins (e.g., proliferative diseases, cardiovascular diseases, viral infections, fibrotic diseases, metabolic diseases, endocrine diseases, and radiation poisoning). The compounds, pharmaceutical compositions, and kits are also useful for male contraception.

  本发明提供了式(I)化合物及其药用组合物。式（I）化合物是溴基链和/或含溴基链蛋白质（如溴外末端（BET）蛋白质）的结合剂。还提供了使用本发明化合物和药物组合物的方法、用途和试剂盒，用于抑制溴基链和/或含溴基链蛋白的活性（如活性增加），治疗和/或预防受试者与溴基链或含溴基链蛋白相关的疾病（如增殖性疾病、心血管疾病、病毒感染、纤维化疾病、代谢性疾病、内分泌疾病和辐射中毒）。这些化合物、药物组合物和试剂盒还可用于男性避孕。
• Asymmetric Michael Addition Reaction of Phosphorus-Stabilized Allyl Anions with Cyclic Enones
  作者：Scott E. Denmark、Jung-Ho Kim

  DOI：10.1021/jo00128a028

  日期：1995.11

  The asymmetric Michael addition reaction of chirally modified P-allyl anions derived from enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides has been investigated with cyclic enones. The racemic 1,3,2-oxazaphosphorinane 2-oxide 3 has been shown to be extremely diastereoselective in the Michael addition to 5-, 6-, and 7-ring enones. With the enantiomerically enriched 2-allyl-1,3,2-oxazaphosphorinane 2-oxides, high regio- and diastereoselectivities (88-90% diastereomeric excess) have been achieved in the Michael addition reaction of one of the diastereomers (cis series). The Michael reaction of the anions derived from the trans series were not diastereoselective (similar to 10% diastereomeric excess). The origin of the addition selectivity can be rationalized by (1) consideration of the structure and conformational preferences of the allyl anion (parallel conformation, s-trans, no lithium contact), (2) conformational analysis of the 1,3,2-oxazaphosphorinane 2-oxide ring (chair, equatorial allyl group) and (3) assumption of a 10-membered ring transition state structure with lithium coordination of the enone.
• Electrophilic activation of the Horner-Wadsworth-Emmons-Wittig reaction: highly selective synthesis of dissymmetric olefins
  作者：Scott E. Denmark、Chien Tien Chen

  DOI：10.1021/ja00052a094

  日期：1992.12
• Alkylation of Chiral, Phosphorus-Stabilized Carbanions: Substituent Effects on the Alkylation Selectivity
  作者：Scott E. Denmark、Chien-Tien Chen

  DOI：10.1021/jo00090a004

  日期：1994.6

  The alkylation of a series of enantiomerically pure cis and trans 3-substituted 2-benzyl-6-methyl-1,3,2-oxazaphosphorinane 2-oxides was found to be sensitive to the bulk of the N-substituents.
• Gordon, Neil J.; Evans, Slayton A., Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 75, # 1-4, p. 47 - 50
  作者：Gordon, Neil J.、Evans, Slayton A.

  DOI：——

  日期：——