(2S,5S)-2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one | 150214-79-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,5S)-2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one
• 英文别名: (2S,5S)-2-t-Butyl-2,5-dimethyl-1,3-dioxolan-4-one；(2S,5S)-2-tert-butyl-2,5-dimethyl-1,3-dioxolan-4-one
• CAS: 150214-79-2
• 化学式: C₉H₁₆O₃
• 分子量: 172.224
• InChiKey: FRRRHODEBCECAT-RCOVLWMOSA-N

物化性质

• 沸点：
  219.3±15.0 °C(Predicted)
• 密度：
  1.001±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,5S)-2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one 在 三异丁基铝 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (2S,5S)-5-tert-Butyl-2,5-dimethyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  New Stereocontrolled Synthesis of Substituted Tetrahydrofurans from 1,3-Dioxolan-4-ones

  摘要：

  DOI：

  10.1021/ja00128a044
• 作为产物：
  描述：

  (1S,2S)-1,2-bis[(4R)-2-tert-butyl-2-methyl-1,3-dioxolan-4-yl]ethane-1,2-diol 在 lead(IV) acetate 、 sodium tetrahydroborate 、 正丁基锂 、 二甲基硫 、 potassium tert-butylate 、 臭氧 、 二异丙胺 作用下， 以 四氢呋喃 、 吡啶 、 六甲基磷酰三胺 、 正己烷 为溶剂， 反应 9.25h， 生成 (2S,5S)-2-(tert-butyl)-2,5-dimethyl-1,3-dioxolan-4-one
  参考文献：
  名称：

  乙醇酸的非竞争性当量：由D-甘露糖醇制备两种对映体

  摘要：

  报道了从D-甘露糖醇开始的2-（叔丁基）-2-甲基-1，3-二氧戊环-4-酮的两种对映异构体的实用合成。这些化合物是乙醇酸的手性当量（=羟基乙酸），其构型稳定并且可以通过其烯醇化物烷基化。

  DOI：

  10.1002/hlca.19960790619

文献信息

• TAXANE COMPOUND WITH AZETIDINE RING STRUCTURE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1942109A1

  公开（公告）日：2008-07-09

  A compound represented by the general formula (1) [X1 and X2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, R1 represents a phenyl group, R2 represents an alkyl group, an alkenyl group, or an alkoxy group, R3 represents hydrogen atom, a halogen atom, hydroxyl group, or an alkoxy group, R4 represents hydrogen atom, or an alkyl group, Z1 and Z2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, Z3 represents cyano group, an alkyl group, an alkenyl group and the like, Z4 represents an alkyl group, an alkenyl group, an alkynyl group and the like, and ---- represents a single bond or a double bond], which shows high antitumor effect against cancer cells including drug resistant cells.

  一个由通式（1）表示的化合物，其中[X1和X2代表氢原子，卤素原子，羟基等，R1代表苯基，R2代表烷基，烯基或烷氧基，R3代表氢原子，卤素原子，羟基或烷氧基，R4代表氢原子或烷基，Z1和Z2代表氢原子，卤素原子，羟基等，Z3代表氰基，烷基，烯基等，Z4代表烷基，烯基，炔基等，----代表单键或双键]，对包括药物耐药细胞在内的癌细胞表现出高抗肿瘤效果。
• (<i>3R</i>)-Chiral Control of 3-Alkyl-3-hydroxy-β-lactams via Addition Reaction of Imines to Enolates of 1,3-Dioxolan-4-ones
  作者：Gaetano Barbaro、Arturo Battaglia、Andrea Guerrini、Carlo Bertucci

  DOI：10.1021/jo9822481

  日期：1999.6.1

  self-regeneration of stereocenters and has been applied to addition reactions among a selected number of imines and (2S)-chiral enolates of 1,3-dioxolan-4-ones. These reagents are easily available from the acetalization of (S)-alpha-hydroxy acids (lactic, mandelic, isovaleric, malic) and pivalaldehyde or pinacolone. In several cases, the addition of the enolate to the imine, the cyclization, and the removal of

  描述了一种以通用且可预测的方式手性构建（3R）-3-烷基-3-羟基-β-内酰胺的方法。该方案遵循Seebach立体中心自我再生的合成原理，并已应用于选定数量的1，3-二氧杂戊环-4-酮亚胺和（2S）-手性烯酸酯之间的加成反应。这些试剂很容易从（S）-α-羟基酸（乳酸，扁桃，异戊酸，苹果酸）和新戊醛或频哪酮的缩醛化中获得。在某些情况下，将烯酸酯添加到亚胺中，环化并去除辅助中心是一步一步完成的，提供了相应的β-内酰胺，如（3R，4S）-Z和（3R，4R ）-E对映体过量的非对映体混合物。四个带有2-呋喃基（4e）的N-未取代的（3R，4S）-3-羟基-3-甲基-β-内酰胺，获得C4处的苯基乙烯基（4h），甲氧基羰基（4i）和2-噻吩基（4l）取代基作为主要的非对映异构体，并通过结晶纯化。这些取代基同时存在于C3和C4处，使这些β-内酰胺成为合成新紫杉烷类的有用中间体，新的紫杉类化合物在异丝氨酸部分具有有趣的结构修饰。
• Synthesis of chiral β2,2,3-3-amino-2-hydroxyalkanoates and 3-alkyl-3-hydroxy-β-lactams by double asymmetric induction
  作者：Andrea Guerrini、Greta Varchi、Rizzo Daniele、Cristian Samorì、Arturo Battaglia

  DOI：10.1016/j.tet.2007.05.069

  日期：2007.8

  Reactions of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic, mandelic, and phenyllactic acids, with aliphatic (SS)- and (SR)-tert-butylsulfinyl aldimines afforded conformationally restrained C2-disubstituted N,O-orthogonally protected 3-amino-2-hydroxyalkanoates in the form of N-sulfinyl protected 1′-aminodioxolan-4-ones. The product distribution showed that there is significant kinetic

  手性（2的反应小号）-enolates二氧戊环-4-酮的，从乳酸，扁桃酸，和phenyllactic酸衍生的，与脂族（小号小号） -和（小号- [R ）-叔丁基亚醛亚胺，得到构象约束C2二取代Ñ，以N-亚磺酰基保护的1'-氨基二氧戊环-4-酮的形式，由O-正交保护的3-氨基-2-羟基链烷酸酯。产物分布表明，由于（S）-或（R）-叔丁基亚砜基亚胺与（2 S）-1,3-二氧戊环-4-酮的烯酸酯。选择性甲醇盐诱导的N-亚磺酰基-1'-氨基二氧戊环酮的缩醛基的去除产生相应的N-亚磺酰基保护的链烷酸甲酯。另外，选择性酸诱导的N-亚磺酰基-1'-氨基二氧杂环戊酮的亚磺酰基的去除提供了相应的N-未保护的1'-氨基二氧杂环戊酮，其碱诱导的环化作用提供了相应的β-内酰胺。
• Taxane Compound Having Azetidine Ring Structure
  申请人：Uoto Kouichi

  公开号：US20090186868A1

  公开（公告）日：2009-07-23

  A compound represented by the general formula (1) [X 1 and X 2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, R 1 represents a phenyl group, R 2 represents an alkyl group, an alkenyl group, or an alkoxy group, R 3 represents hydrogen atom, a halogen atom, hydroxyl group, or an alkoxy group, R 4 represents hydrogen atom, or an alkyl group, Z 1 and Z 2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, Z 3 represents cyano group, an alkyl group, an alkenyl group and the like, Z 4 represents an alkyl group, an alkenyl group, an alkynyl group and the like, and represents a single bond or a double bond], which shows high antitumor effect against cancer cells including drug resistant cells.

  一种化合物由通式（1）表示 [其中X1和X2代表氢原子、卤素原子、羟基等，R1代表苯基，R2代表烷基、烯基或烷氧基，R3代表氢原子、卤素原子、羟基或烷氧基，R4代表氢原子或烷基，Z1和Z2代表氢原子、卤素原子、羟基等，Z3代表氰基、烷基、烯基等，Z4代表烷基、烯基、炔基等，且表示单键或双键]，对包括耐药细胞在内的癌细胞具有高抗肿瘤效果。
• The first synthesis of N,O-protected β2,2,3,3-isoserines bearing two adjacent quaternary stereogenic centers and their corresponding β-lactams
  作者：Andrea Guerrini、Greta Varchi、Cristian Samorì、Rizzo Daniele、Battaglia Arturo

  DOI：10.1016/j.tetlet.2007.05.087

  日期：2007.7

  The reaction of chiral (2S)-enolates of dioxolan-4-ones, derived from lactic and mandelic acids, with (S-R,?)-tert-butyl sulfinyl ketimines, derived from butan-2-one, pentan-2-one, and decan-2-one, afforded conformation ally restrained beta(2,2,3,3) -isoserines bearing two adjacent quaternary stereogenic centers in the form of N-sulfinyl protected 1'-amino-dioxolan-4-ones. The selective acid-induced removal of the sulfinyl protecting group provided the corresponding 1'-aminodioxolanones, whose base-induced cyclization afforded the corresponding chiral tetra-substituted 3-hydroxy-beta-lactams. The synthesis of a dipeptide by reaction coupling between the 1'-aminodioxolanone (2S,5R,1'R)-19 and N,N-dimethylglycine was successfully achieved. (C) 2007 Elsevier Ltd. All rights reserved.