[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone | 16354-97-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone
• 英文别名: [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-phenylmethanone
• CAS: 16354-97-5
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: KKHRYPWZVRWBOJ-SNVBAGLBSA-N

物化性质

• 熔点：
  50-52 °C
• 沸点：
  296.6±35.0 °C(Predicted)
• 密度：
  1.107±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  [(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone 在 盐酸 作用下， 生成 (R)-2,3-dihydroxy-1-phenylpropan-1-one
  参考文献：
  名称：

  Synthesis of optically active 1-C-phenylglycerols and their derivatives

  摘要：

  DOI：

  10.1021/jo01270a066
• 作为产物：
  描述：

  (R)-(+)-2,2-二甲基-1,3-二氧戊环-4-甲醛 生成 [(R)-2,2-dimethyl-1,3-dioxolan-4-yl]phenylmethanone
  参考文献：
  名称：

  CHIKASHITA, HIDENORI;NIKAYA, TOSHIKI;UEMURA, HIROMITSU;ITOH, KAZUYOSHI, BULL. CHEM. SOC. JAP., 62,(1989) N, C. 2121-2123

  摘要：

  DOI：

文献信息

• Heteroatom-Guided Torquoselective Olefination of α-Oxy and α-Amino Ketones via Ynolates
  作者：Mitsuru Shindo、Takashi Yoshikawa、Yasuaki Itou、Seiji Mori、Takeshi Nishii、Kozo Shishido

  DOI：10.1002/chem.200500574

  日期：2006.1

  Ynolates were found to react with alpha-alkoxy-, alpha-siloxy-, and alpha-aryloxyketones at room temperature to afford tetrasubstituted olefins with high Z selectivity. Since the geometrical selectivity was determined in the ring opening of the beta-lactone enolate intermediates, the torquoselectivity was controlled by the ethereal oxygen atoms. From experimental and theoretical studies, the high Z

  发现壬酸酯在室温下与α-烷氧基-，α-甲硅烷氧基-和α-芳氧基酮反应，得到具有高Z选择性的四取代的烯烃。由于几何选择性是在β-内酯烯醇中间体的开环中确定的，因此torquoselectivity由醚性氧原子控制。从实验和理论研究来看，高Z选择性是由轨道和空间相互作用而不是由螯合引起的。以类似的方式，α-二烷基氨基酮为烯烃提供了优异的Z选择性。这些产物可以容易地以良好的产率转化为多取代的丁烯内酯和γ-丁内酰胺。
• Further Uses of Pyrrole-Based Dienoxysilane Synthons: A Full Aldol Approach to Azabicyclo[x.2.1]alkane Systems
  作者：Franca Zanardi、Claudio Curti、Andrea Sartori、Gloria Rassu、Annamaria Roggio、Lucia Battistini、Paola Burreddu、Luigi Pinna、Giorgio Pelosi、Giovanni Casiraghi

  DOI：10.1002/ejoc.200800040

  日期：2008.5

  bond-forming reactions, the efficiencies of which were secured by appropriate aldol-stabilizing steps. A mechanistic rationale accounting for the markedly diastereoselective character of the key Mukaiyama aldol reactions between TBSOP and the ketone acceptors has been postulated that involves hetero-Diels-Alder transition-state structures in which the preference for endo versus exo addition is governed by

  从 1-（叔丁氧基羰基）开始合成了两个外消旋 2-氮杂双环 [2.2.1] 庚烷结构 15 和 21 和两个手性非外消旋 6-氮杂双环 [3.2.1] 辛烷代表 28 和 36 -2-（叔丁基二甲基甲硅烷氧基）吡咯（TBSOP，5）和合适的酮，9、16、22 和 29。然后将 2-氮杂双环 15 加工成外消旋环戊烷氨基酸 38，而 6-氮杂双环 36 用于获得对映异构纯的去甲吗喃型结构 40。对于所有底物，基于两种非对映选择性羟醛型碳-碳键形成反应的组合实施了统一的合成方案，其效率通过适当的羟醛稳定步骤来保证。
• Stereoselective<i>syn</i>-Reduction of (<i>R</i>)-4-Acyl-2,2-dimethyl-1,3-dioxolanes with Metal Hydride Reagents
  作者：Hidenori Chikashita、Toshiki Nikaya、Hiromitsu Uemura、Kazuyoshi Itoh

  DOI：10.1246/bcsj.62.2121

  日期：1989.6

  Lithium tri-s-butylborohydride and lithium aluminum hydride were found to be efficient reducing agents for the stereoselective preparation of syn-glycerol derivatives from (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes. The scope and limitation of the stereoselective L-Selectride reduction of (R)-4-acyl-2,2-dimethyl-1,3-dioxolanes were also described.

  发现三叔丁基硼氢化锂和氢化铝锂是从 (R)-4-酰基-2,2-二甲基-1,3-二氧戊环立体选择性制备合成甘油衍生物的有效还原剂。还描述了 (R)-4-酰基-2,2-二甲基-1,3-二氧戊环的立体选择性 L-Selectride 还原的范围和限制。
• A Route to Homochiral (S)-<u>O</u>-Methyl Mandelic Acid and Related α-Alkoxy Carboxylic Acids from Isopropylidene Glycerol
  作者：Sheetal Handa、John E. Hawes、Robert J. Pryce

  DOI：10.1080/00397919508011831

  日期：1995.9

  An improved synthesis of the useful ketones 7 is described. These ketones are then further modified via a highly stereospecific reduction. to give homochiral alpha-alkoxy carboxylic acids which are useful chiral auxiliaries and intermediates.
• Vicarious Silylative Mukaiyama Aldol Reaction: A Vinylogous Extension
  作者：Claudio Curti、Andrea Sartori、Lucia Battistini、Gloria Rassu、Paola Burreddu、Franca Zanardi、Giovanni Casiraghi

  DOI：10.1021/jo800741c

  日期：2008.7.1

  A vinylogous, silylative, and direct variant of the venerable Mukaiyama aldol reaction has been developed. Exploiting N-Boc-pyrrol-2(5H)-one as the conjugate donor, several aldehyde and ketone acceptors were scrutinized under the guidance of suitable dual Lewis acid-Lewis base activators to provide a varied repertoire of functionality-rich alpha,beta-unsaturated-gamma-amino-delta-silyloxy carbonyl structures, in useful yields and often with an exquisite level of diastereoselection.