((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-nonyl-[1,3]dithian-2-yl)-methanone | 123695-73-8

• 分子结构分类: 有机化合物
• 英文名称: ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-nonyl-[1,3]dithian-2-yl)-methanone
• 英文别名: [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-(2-nonyl-1,3-dithian-2-yl)methanone
• CAS: 123695-73-8
• 化学式: C₁₉H₃₄O₃S₂
• 分子量: 374.609
• InChiKey: ZRGTYRCKKWLVIJ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  86.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-nonyl-[1,3]dithian-2-yl)-methanone 生成 (S)-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-(2-nonyl-[1,3]dithian-2-yl)-methanol
  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：
• 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)-(2-nonyl-[1,3]dithian-2-yl)-methanone
  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

• 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。
• Highly Diastereoselective Addition of Methyllithium to Chiral α,β-Dialkoxy Ketones and Its Application to the Stereocontrolled Asymmetric Synthesis of Highly Substituted Tetrahydrofurans
  作者：Hidenori Chikashita、Yusuke Nakamura、Hiromitsu Uemura、Kazuyoshi Itoh

  DOI：10.1246/cl.1992.439

  日期：1992.3

  The nucleophilic addition of methyllithium to chiral α,β-dialkoxy 1,3-dithian-2-yl ketones in ether gave the corresponding Cram type of anti isomers in excellent diastereoselectivity. The method was applied to the stereocontrolled synthesis of optically active and highly substituted tetrahydrofurans.

  甲基锂与手性 α,β-二烷氧基 1,3-二噻烷-2-基酮在醚中的亲核加成得到相应的 Cram 类型的反异构体，具有优异的非对映选择性。该方法用于立体控制合成光学活性和高度取代的四氢呋喃。
• Stereocontrolled 1,4-Asymmetric Reduction of Cyclic Hemiketals. Synthesis of Both<i>anti</i>and<i>syn</i>-1,4-Diols, and Their Transformations into<i>trans</i>-and<i>cis</i>-2,5-Disubstituted Tetrahydrofurans
  作者：Hidenori Chikashita、Takashi Fukushima、Hiromitsu Uemura、Kazuyoshi Itoh

  DOI：10.1246/cl.1992.599

  日期：1992.4

  Reduction of dithioacetal-functionalized cyclic hemiketals with LiAlH4 in THF and NaBH4 in ethanol gave the corresponding anti- and syn-1,4-diols with excellent Stereoselectivity, respectively. The anti- and syn-1,4-diols were easily transformed into trans- and cis-2,5-disubstituted tetrahydrofurans with complete stereospecificity by the one-step cyclodehydration with p-TsCl in pyridine, respectively

  在 THF 中用 LiAlH4 和在乙醇中的 NaBH4 还原二硫缩醛官能化的环状半缩酮，分别得到相应的具有优异立体选择性的反和顺-1,4-二醇。通过在吡啶中用 p-TsCl 进行一步环脱水，反式和顺式 1,4-二醇很容易转化为具有完全立体特异性的反式和顺式 2,5-二取代四氢呋喃。