bromo-[1-14C]acetic acid methyl ester | 13855-81-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: bromo-[1-14C]acetic acid methyl ester
• 英文别名: bromo-[1-¹⁴C]acetic acid methyl ester
• CAS: 13855-81-7
• 化学式: C₃H₅BrO₂
• 分子量: 154.964
• InChiKey: YDCHPLOFQATIDS-YZRHJBSPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.55
• 重原子数：
  6.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  bromo-[1-14C]acetic acid methyl ester 在 aluminium hydride 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以50%的产率得到2-bromo[1-14C]ethanol
  参考文献：
  名称：

  Synthesis of 4-tert-butyl-3-(2-chloro -[-2-14C]ethyl)ureido benzene

  摘要：

  Carbonation of CH3MgI with (CO2)-C-14 led to sodium [1-C-14] acetate: (1) under bar which was successively brominated and esterifed with diazomethane to give rise to methyl 2-bromo-[-1-C-14] acetate: (3) under bar, the reduction of which with H3Al gave 2-bromo-[-1-C-14] ethanol (4) under bar. (4) under bar was then reacted with NaCN; the intermediate 3-hydroxy-[-3-C-14] propionitrile (5) under bar was hydrolyzed with HCL at 130 degrees C into the corresponding acid: (6) under bar which was transformed into 3-chloro-[-3-C-14] propionyl chloride: (7) under bar;(7) under bar reacted with NaN3 gave 3-chloro-[-3-C-14] propyl azide: (8) under bar which by Curtius rearrangment led to 2-chloro-[-2-C-14] ethyl isocyanate: (9) under bar which finally was condensed with 4-t-butylaniline leading to the title compound (radiochemical purity 99%) in an overall yield of about 10% based on [C-14] barium carbonate.

  DOI：

  10.1002/(sici)1099-1344(199707)39:7<559::aid-jlcr4>3.0.co;2-3
• 作为产物：
  描述：

  重氮甲烷 、 [1-¹⁴C]bromoacetic acid 以 乙醚 为溶剂， 生成 bromo-[1-14C]acetic acid methyl ester
  参考文献：
  名称：

  不同位置放射性碳标记的德兰环烷的合成

  摘要：

  [U- 14 C]溴苯，根据文献方法由[ 14 C]碳酸钡制备，转化（Li/二乙醚）为[ 14 C]苯基锂，后者与樟脑缩合生成[U- 14 C-苯基]冰片：2。后者在转化为其钠盐后，与二甲氨基乙基氯反应，得到[ 14 C-Ar]德环环烷，将其作为富马酸盐分离。这种由[ 14 C]BaCO 3 的8步合成得到12%的总产率。[1- 14 C]乙酸钠，通过标准的 5 步文献程序，被转化为 N,N-二甲氨基乙基-1- 14 C 氯化物 5，后者与 2-苯基冰片的钠衍生物缩合生成 [1- 14 C-侧链]Deramciclane，再次分离为富马酸盐。这种由[ 14 C]BaCO 3 的6步合成得到8％的总产率。两种合成的比放射性分别为40 mCi/mmol和21 mCi/mmol；化学和放射化学纯度均优于 98%。

  DOI：

  10.1002/(sici)1099-1344(199712)39:12<1011::aid-jlcr49>3.0.co;2-z

文献信息

• Interconversion and cyclization of acyclic allylic pyrophosphates in the biosynthesis of cyclic monoterpenoids in higher plants
  作者：Takayuki Suga、Toshifumi Hirata、Tadashi Aoki、Tsuyoshi Shishibori

  DOI：10.1016/s0031-9422(00)83738-3

  日期：1986.1

  The biosynthesis of cyclic monoterpenoids has been investigated in both intact plants and cell-free extracts of several higher plants. The participation of a non-redox process in the biosynthesis of the cyclic monoterpenoids was indicated by the retention of all the tritium labels originating from [2- 14 C,5- 3 H 2 ]mevalonic acid and [1- 14 C,1- 3 H 2 ]geranyl, neryl and linalyl pyrophosphates. The

  摘要 环状单萜类化合物的生物合成已在几种高等植物的完整植物和无细胞提取物中进行了研究。通过保留所有源自 [2- 14 C,5- 3 H 2 ] 甲羟戊酸和 [1- 14 C,1- 3 H 2 ]香叶基、橙花基和芳樟基焦磷酸酯。无细胞提取物催化香叶基、橙花基和焦磷酸芳樟基相互之间的非氧化还原相互转化。相比之下，在完整植物和无细胞提取物中，焦磷酸芳樟酯掺入环状单萜类化合物的发生优先于橙花酯和香叶基焦磷酸酯掺入。
• Synthesis of [7-¹⁴C]bergapten
  作者：Crist N. Filer、Thomas Rodgers

  DOI：10.1002/jlcr.3172

  日期：2014.2

  Bergapten (1) is a furocoumarin natural product and currently employed to treat skin disorders. Since past attempts to radiolabel 1 with 14C were limited to only its 5‐methoxy group, a synthesis of the required ring [7‐14C]1 is now described. The literature reported precursor 4‐methoxy‐6‐hydroxybenzofuran‐5‐carboxaldehyde (3) was Wittig reacted with stabilized [carbonyl‐14C]methoxycarbonylmethylen

  Bergapten（1）是呋喃香豆素的天然产品，目前用于治疗皮肤疾病。由于过去尝试用14 C标记1的尝试仅限于其5-甲氧基，因此现在描述所需环[ 7-14 C] 1的合成。文献报道前体4-甲氧基-6-羟基苯并呋喃-5-甲醛（3）与Wittig与稳定的[羰基14 C]甲氧基羰基亚甲基三苯基磷烷（4）反应得到[ 7-14 C] 1，放射化学产率为47％，通过薄层色谱，HPLC，mp和质子NMR对所需产物进行表征。
• Orsini, Fulvia; Pelizzoni, Francesca, Gazzetta Chimica Italiana, 1980, vol. 110, # 9/10, p. 553 - 556
  作者：Orsini, Fulvia、Pelizzoni, Francesca

  DOI：——

  日期：——