3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoic acid | 111192-54-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoic acid
• CAS: 111192-54-2
• 化学式: C₈H₁₄O₄
• 分子量: 174.197
• InChiKey: VOIMKESBBFHOSH-LURJTMIESA-N

物化性质

• 沸点：
  266.1±20.0 °C(Predicted)
• 密度：
  1.103±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoic acid 在 lithium aluminium tetrahydride 作用下， 生成 3-[(4S)-2,2-二甲基-1,3-二氧戊烷-4-基]-丙醇
  参考文献：
  名称：

  （+）-rolliniastatin 1的全合成

  摘要：

  天然的产乙酸素（+）-rolliniastatin 1（1）的第一个全合成已经实现。通过将由5和11衍生的官能化有机金属试剂螯合控制地添加到α-烷氧基-醛中，可以实现bis-THF系统构建过程中的高度立体化学控制。

  DOI：

  10.1016/s0040-4039(00)77159-0
• 作为产物：
  描述：

  3-[(4S)-2,2-二甲基-1,3-二氧戊烷-4-基]-丙醇 在 potassium bromide 4-(polystyrylMeO)-2,2,6,6-tetraMepiperidin-1-yloxy radical 、 PS-CH₂Me₃(+)*ClO₂(-) 、 PS-CH₂NMe₃(+)*H₂PO₄(-) 作用下， 以 水 、 乙腈 为溶剂， 反应 36.0h， 以76%的产率得到3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]propanoic acid
  参考文献：
  名称：

  The simultaneous use of immobilised reagents for the one-pot conversion of alcohols to carboxylic acids

  摘要：

  在单个反应容器中同时使用选定的固定氧化试剂，是将伯醇转化为相应羧酸的有效方法。

  DOI：

  10.1039/b201776h

文献信息

• Stereoselective total synthesis of cananginones (D–I) using Ireland–Claisen rearrangement as a key step
  作者：Tapan Kumar Kuilya、Shamba Chatterjee、Rajib Kumar Goswami

  DOI：10.1016/j.tet.2014.03.028

  日期：2014.5

  A strategy for stereoselective total synthesis of α-substituted γ-hydroxymethyl γ-butyrolactone containing bioactive natural products cananginones (D–I) has been developed using cheap and commercially available d-mannitol as a chiral pool. The Ireland–Claisen rearrangement is utilized as a key step to generate the α-substituted chiral center of the core lactone moiety, while the elongation of aliphatic

  已经开发了一种使用廉价的市售d-甘露糖醇作为手性库的立体选择性全合成含有生物活性天然产物cananginones（D–I）的α-取代的γ-羟甲基γ-丁内酯的策略。爱尔兰-克莱森重排被用作生成核心内酯部分的α-取代手性中心的关键步骤，而烷基化，Cadiot-Chodkiewicz和Sonogashira反应。
• Total synthesis of (+)-rolliniastatin 1
  作者：Ulrich Koert

  DOI：10.1016/s0040-4039(00)77159-0

  日期：1994.4

  The first total synthesis of the naturally occurring acetogenin (+)-rolliniastatin 1 (1) has been achieved. A high degree of stereochemical control in the construction of the bis-THF system was accomplished by chelation controlled addition of functionalized organo-metallic reagents derived from 5 and 11 to α-alkoxy-aldehydes.

  天然的产乙酸素（+）-rolliniastatin 1（1）的第一个全合成已经实现。通过将由5和11衍生的官能化有机金属试剂螯合控制地添加到α-烷氧基-醛中，可以实现bis-THF系统构建过程中的高度立体化学控制。
• A diastereoselective synthesis of (S,S)-α-fluoro-2,2-dimethyl-1,3-dioxolane-4-propanoic acid methyl ester, a key intermediate for the preparation of anti-HIV effective fluorodideoxynucleosides
  作者：Maqbool A. Siddiqui、Victor E. Marquez、John S. Driscoll、Joseph J. Barchi

  DOI：10.1016/s0040-4039(00)76880-8

  日期：1994.5

  anti-HIV active 9-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)adenine (1, FddA) and 1-(2,3-dideoxy-2-fluoro-β-D-threo-pentofuranosyl)cytosine (2, FddC) was prepared via the diastereoselective fluorination of the chiral imide enolate obtained from 8 with N-fluorobenzenesulfonimide. The overall yield of 10 from the readily available 1,2:5,6-di-O-isopropylidene-D-mannitol was 25% (de 93%).

  （S，S）-α-氟-2,2-二甲基-1,3-二氧戊环-4-丙酸甲酯（10），是制备抗HIV活性9-（2,3-的关键中间体制备了二脱氧-2-氟-β-D-苏-戊呋喃糖基）腺嘌呤（1，FddA）和1-（2,3-二脱氧-2-氟-β-D-苏-戊呋喃糖基）胞嘧啶（2，FddC）通过由N-氟苯磺酰亚胺从8获得的手性酰亚胺烯醇的非对映选择性氟化。容易获得的1,2：5,6-二-O-异亚丙基-D-甘露糖醇的总收率为10％，为25％（de 93％）。
• Methods for synthesis of substituted tetrahydrofuran compound
  申请人：——

  公开号：US20020035278A1

  公开（公告）日：2002-03-21

  The invention includes inter alia new methods for preparation of the pharmaceutically active compound 2-(4-fluorophenoxymethyl)-5-(4-N-hydroxyureidyl-1-butynyl)-tetrahydrofuran and precursors thereof

  本发明主要包括制备药物活性化合物 2-(4-氟苯氧甲基)-5-(4-N-羟基脲基-1-丁炔基)-四氢呋喃及其前体的新方法
• RCM-Based Synthesis of a Variety of β-<i>C</i>-Glycosides and Their in Vitro Anti-Solid Tumor Activity
  作者：Maarten H. D. Postema、Jared L. Piper、Russell L. Betts、Frederick A. Valeriote、Halina Pietraszkewicz

  DOI：10.1021/jo040254t

  日期：2005.2.1

  The synthesis of a number of biologically relevant C-glycosides has been carried out through the use of an esterification-ring-closing metathesis (RCM) strategy. The required acid precursors were readily prepared via a number of standard chemical transformations followed by dehydrative coupling of these acids with several olefin alcohols 1 to yield the precursor esters 3 in excellent yield. Methylenation of the esters 3 was followed by RCM and in situ hydroboration-oxidation of the formed glycals to furnish the protected beta-C-glycosides 6 in good overall yield. Several examples were converted to the corresponding C-glycoglycerolipids 17 and subsequently screened against solid-tumor cell lines for in vitro differential cytotoxicity.