(3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one | 160408-99-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
• 英文别名: (3R,4S)-3-Benzyloxy-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-2-azetidinone；(3R,4S)-4-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-phenylmethoxyazetidin-2-one
• CAS: 160408-99-1
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: LUYRYTPDHIPFOT-FRRDWIJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 、 乙醚 、 乙腈 为溶剂， 生成 [(1S,2R)-2-Benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-3-ethyl-3-hydroxy-pentyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Concise General Synthesis of .alpha.,.gamma.-Disubstituted .beta.-Amino Ketones from .beta.-Lactams

  摘要：

  alpha,gamma-Disubstituted beta-amino ketones were obtained by ring opening of 3,4-disubstituted N-Boc-beta-lactams, promoted by Grignard and organocuprate reagents.

  DOI：

  10.1021/jo00097a020
• 作为产物：
  描述：

  苄氧基乙酰氯 在 臭氧 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 苯 为溶剂， 反应 13.5h， 生成 (3R,4S)-3-(Benzyloxy)-4-<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>azetidin-2-one
  参考文献：
  名称：

  2,3-Diaza-1,3-dienes (Azines) as Substrates for the Staudinger Reaction. Synthesis and Reactivity of N-Imino-.beta.-lactams

  摘要：

  The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et(3)N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-beta-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-beta-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-beta-lactams, The usual reactivity of the beta-lactam ring is modified in N-imino-beta-lactams by the presence of the imino group. Thus, beta-hydrazonoesters, N-alkylamino-beta-lactams, and NH-beta-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.

  DOI：

  10.1021/jo00105a014

文献信息

• Synthesis and Biological Evaluation of C-3'-Modified Analogs of 9(R)-Dihydrotaxol
  作者：Leping Li、Sheela A. Thomas、Larry L. Klein、Clinton M. Yeung、Clarence J. Maring、David J. Grampovnik、Paul A. Lartey、Jacob J. Plattner

  DOI：10.1021/jm00043a005

  日期：1994.8

  Taxol (1) is considered a most exciting new drug in cancer chemotherapy. The promising antitumor activity of 9(R)-dihydrotaxol (3) encouraged us to further explore the structure-activity relationship of this new member of the taxane family. Studies indicated that the C-13 side chain of taxol is indispensable for antitumor activity and that the natural substitution pattern of a 2'(R)-hydroxy and a 3'(S)-acylamino

  紫杉醇（1）被认为是癌症化疗中最令人兴奋的新药。9（R）-二氢紫杉醇（3）的有希望的抗肿瘤活性鼓励我们进一步探索紫杉烷家族这个新成员的结构-活性关系。研究表明，紫杉醇的C-13侧链对于抗肿瘤活性是必不可少的，并且2'（R）-羟基和3'（S）-酰氨基的天然取代方式可能是最佳的。然而，关于3'-苯环对活性的影响了解的很少。描述了在C-3'位置修饰的3的类似物的合成和生物学评估。这项研究表明3'-苯环不是活性所必需的，并鉴定了几种在体外和体内活性均与紫杉醇相同或更高的化合物。
• 2,3-Diaza-1,3-dienes (Azines) as Substrates for the Staudinger Reaction. Synthesis and Reactivity of N-Imino-.beta.-lactams
  作者：Benito Alcaide、Miguel Miranda、Javier Perez-Castells、Concepcion Polanco、Miguel A. Sierra

  DOI：10.1021/jo00105a014

  日期：1994.12

  The reaction of aromatic and aliphatic azines with different ketene precursors, such as the acid chloride/Et(3)N system, alkoxychromium(0) carbenes, and free diphenyl ketene, gives N-imino-beta-lactams in good to excellent yields, with good levels of cis,trans-selectivity. A wide variety of symmetrically-substituted azines derived from aldehydes and ketones are compatible with the Staudinger reaction. Chiral N-imino-beta-lactams derived from symmetrically or unsymmetrically (mixed) chiral azines are also obtained in good yields as essentially single enantiomers (de > 95%). Different reaction intermediates, including hemiaminals, oxadiazols, and hydrazides have been isolated. Free diphenyl ketene forms Diels-Alder adducts and N-acylazadienes in addition to the previously reported N-imino-beta-lactams, The usual reactivity of the beta-lactam ring is modified in N-imino-beta-lactams by the presence of the imino group. Thus, beta-hydrazonoesters, N-alkylamino-beta-lactams, and NH-beta-lactams can be efficiently obtained by base-catalyzed 2-azetidinone ring opening, catalytic hydrogenation, and ozonolysis, respectively.
• Concise General Synthesis of .alpha.,.gamma.-Disubstituted .beta.-Amino Ketones from .beta.-Lactams
  作者：Claudio Palomo、Jesus M. Aizpurua、Jesus M. Garcia、Miren Iturburu、Jose M. Odriozola

  DOI：10.1021/jo00097a020

  日期：1994.9

  alpha,gamma-Disubstituted beta-amino ketones were obtained by ring opening of 3,4-disubstituted N-Boc-beta-lactams, promoted by Grignard and organocuprate reagents.